Post on 24-Oct-2014
Task HistoryMay 24, 2011 2:45 PMExplore reactions by structure variable only at specified positions structure initiated Query
Explore completeExplore resultsAnswer set 11 created with 65 reactions
SciFinder® Page 1
1. Single Step
90%
Overview
Steps/Stages Notes
1.1 R:PPh3, S:MeCN, 15 min, rt1.2 R: 1 h, 40°C
Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 2, Most stages in any one step: 2
ReferencesSynthesis of benzyl bromides withhexabromoacetone: an alternative path todrug intermediatesBy Joseph, Kara M., Larraza-Sanchez, IsabelFrom Tetrahedron Letters, 52(1), 13-16; 2011
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.2. Single Step
100%
Overview
Steps/Stages Notes
1.1 R:PPh3, S:MeCN, 15 min, rt1.2 R: overnight, rt
1) optimization study (optimized on solventand temperature), Reactants: 1, Reagents: 2,Solvents: 1, Steps: 1, Stages: 2, Most stagesin any one step: 2
ReferencesSynthesis of benzyl bromides withhexabromoacetone: an alternative path todrug intermediatesBy Joseph, Kara M., Larraza-Sanchez, IsabelFrom Tetrahedron Letters, 52(1), 13-16; 2011
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.3. Single Step
SciFinder® Page 2
75%
Overview
Steps/Stages Notes
1.1 R:PBr3, S:THF, 5 min, rt 1) alternative reaction conditions shown,polyimide film microreactor used, Reactants: 1,Reagents: 1, Solvents: 1, Steps: 1, Stages: 1,Most stages in any one step: 1
ReferencesMonolithic and Flexible Polyimide FilmMicroreactors for Organic MicrochemicalApplications Fabricated by Laser AblationBy Min, Kyoung-Ik et alFrom Angewandte Chemie, InternationalEdition, 49(39), 7063-7067, S7063/1-S7063/3; 2010
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.4. Single Step
76%
Overview
Steps/Stages Notes
1.1 R:Br2, R:PPh3, S:CH2Cl2, 0°C; 30 min, 0°C
1.2 3 h, 0°C
Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 2, Most stages in any one step: 2
ReferencesIdentification and biosynthesis of troponederivatives and sulfur volatiles produced bybacteria of the marine Roseobacter cladeBy Thiel, Verena et alFrom Organic & Biomolecular Chemistry,8(1), 234-246; 2010
SciFinder® Page 3
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.5. Single Step
94%
Overview
Steps/Stages Notes
1.1 R:KBr, C:H2SO4, S:H2O, 20 min, heated; 4 h, reflux 1) optimization study, optimized onstoichiometry, catalyst and solvent amount,time, Reactants: 1, Reagents: 1, Catalysts: 1,Solvents: 1, Steps: 1, Stages: 1, Most stagesin any one step: 1
ReferencesSynthesis of benzyl bromide using potassiumbromide and concentrated sulfuric acidmethodBy Song, Zhiguo et alFrom Gongye Cuihua, 16(1), 48-50; 2008
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.6. Single Step
94%
Overview
Steps/Stages Notes
1.1 R:H2SO4, R:KBr, S:H2O, 20 min, reflux; 4 h, reflux Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesClean synthesis and characterization ofbromoalkanesBy Song, Zhiguo et alFrom Jingxi Huagong Zhongjianti, 38(1), 37-39; 2008
SciFinder® Page 4
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.7. Single Step
86%
Overview
Steps/Stages Notes
1.1 R:Br2, R:PPh3, R:1H-Imidazole, S:CH2Cl2, 0°C; 0°C → 22°C Reactants: 1, Reagents: 3, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesN-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)arylamide as a New Scaffold thatProvides Rapid Access to AntimicrotubuleAgents: Synthesis and Evaluation ofAntiproliferative Activity Against SelectCancer Cell LinesBy Stefely, Jonathan A. et alFrom Journal of Medicinal Chemistry, 53(8),3389-3395; 2010
Experimental Procedure9a, yield 86%
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.8. Single Step
80%
Overview
Steps/Stages Notes
SciFinder® Page 5
1.1 R:PBr3, S:CH2Cl2, 1 h, 0°C; 15 h, 20°C Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesCollision-induced loss of AgH from Ag+adducts of alkylamines, aminocarboxylicacids and alkyl benzyl ethers leadsexclusively to thermodynamically favoredproduct ionsBy Schaefer, Mathias et alFrom Journal of Mass Spectrometry, 44(2),278-284; 2009
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.9. Single Step
polymer-supported polymer-supported93%
Overview
Steps/Stages Notes
1.1 R:PBr3, S:CH2Cl2, 0°C → rt Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesA Yb(OTf)3/PEG-supported quaternaryammonium salt catalyst system for a three-component Mannich-type reaction in aqueousmediaBy Hong, Deng et alFrom Synlett, (7), 1107-1110; 2009
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.10. Single Step
98%
Overview
Steps/Stages Notes
SciFinder® Page 6
1.1 R:Cyanurictrichloride, S:DMF, 25°C
1.2 R:NaBr, S:CH2Cl2, 10 h, 25°C
1.3 15 min, rt
Reactants: 1, Reagents: 2, Solvents: 2, Steps:1, Stages: 3, Most stages in any one step: 3
ReferencesA chemoselective, easy bromination of(hydroxymethyl)phenolsBy Nieddu, Giammario et alFrom Synthesis, (24), 3937-3940; 2008
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.11. Single Step
60%
Overview
Steps/Stages Notes
1.1 R:LiBr, R:PPh3, R:EtO2CN=NCO2Et, R:N2(CO2CHMe2)2, S:THF 1) PPh3, DEAD or DIAD, LiBr, THF, 0 C,Bromination, Halogenation, Substitution,Reactants: 1, Reagents: 4, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesThe Mitsunobu reactionBy Hughes, David L.From Organic Reactions (Hoboken, NJ,United States), 42(), No pp. given; 1992
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.12. Single Step
91%
Overview
Steps/Stages Notes
SciFinder® Page 7
1.1 R:
R:PPh3,R:EtO2CN=NCO2Et,R:N2(CO2CHMe2)2,
S:THF 1) PPh3, DEAD or DIAD, MeBr/MTD, THF,r.t./6 h., Bromination, Halogenation,Substitution, Reactants: 2, Reagents: 4,Solvents: 1, Steps: 1, Stages: 1, Most stagesin any one step: 1
ReferencesThe Mitsunobu reactionBy Hughes, David L.From Organic Reactions (Hoboken, NJ,United States), 42(), No pp. given; 1992
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.13. Single Step
76%
Overview
Steps/Stages Notes
1.1 R:Ph3PBr2, S:CCl41) Ph3PBr2, CCl4, 80 C/20 min., Bromination,Halogenation, Substitution, Reactants: 1,Reagents: 1, Solvents: 1, Steps: 1, Stages: 1,Most stages in any one step: 1
ReferencesReplacement of alcoholic hydroxyl groups byhalogens and other nucleophiles viaoxyphosphonium intermediatesBy Castro, Bertrand R.From Organic Reactions (Hoboken, NJ,United States), 29(), No pp. given; 1983
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.14. Single Step
SciFinder® Page 8
Overview
Steps/Stages Notes
1.1 C:Et3SiH, C:PdCl2, C:CH2Br21) Additional Ionic Hydrogenation andReductive Substitutions, Reactants: 1,Catalysts: 3, Steps: 1, Stages: 1, Most stagesin any one step: 1
ReferencesTriethylsilaneBy Fry, James L. et alFrom e-EROS Encyclopedia of Reagents forOrganic Synthesis, (), No pp. given; 2001
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.15. Single Step
98%
Overview
Steps/Stages Notes
1.1 R:
R:PPh3,
S:CH2Cl2, 15 min, rt Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesHexabromoacetone and ethyltribromoacetate: a highly efficient reagent forbromination of alcoholBy Tongkate, Pratoomrat et alFrom Tetrahedron Letters, 49(7), 1146-1148;2008
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.16. Single Step
92%
SciFinder® Page 9
Overview
Steps/Stages Notes
1.1 R:HBr, S:PhCH2OH, 4 h, reflux Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesSimple synthesis of fresh alkyl iodides usingalcohols and hydriodic acidBy Klein, Suzane M. et alFrom Tetrahedron Letters, 49(16), 2638-2641; 2008
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.17. Single Step
80%
Overview
Steps/Stages Notes
1.1 R:Br2, R:PPh3, S:MeCN, 2 h, 55°C Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesAn unprecedented rearrangement in collision-induced mass spectrometric fragmentation ofprotonated benzylaminesBy Bialecki, Jason et alFrom Journal of Mass Spectrometry, 41(9),1195-1204; 2006
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.18. Single Step
SciFinder® Page 10
80%
Overview
Steps/Stages Notes
1.1 R:Br2, R:PPh3, S:MeCN, 2 h, 55°C Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesAn unprecedented rearrangement in collision-induced mass spectrometric fragmentation ofprotonated benzylaminesBy Bialecki, Jason et alFrom Journal of Mass Spectrometry, 41(9),1195-1204; 2006
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.19. Single Step
80%
Overview
Steps/Stages Notes
1.1 R:Br2, R:PPh3, S:MeCN, 2 h, 55°C Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesAn unprecedented rearrangement in collision-induced mass spectrometric fragmentation ofprotonated benzylaminesBy Bialecki, Jason et alFrom Journal of Mass Spectrometry, 41(9),1195-1204; 2006
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.20. Single Step
SciFinder® Page 11
70%
Overview
Steps/Stages Notes
1.1 S:CH2Cl2, rt → -40°C
1.2 R:BBr3, 15 min, -40°C; 30 min, 0°C
Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 2, Most stages in any one step: 2
ReferencesMaking a Difference on Excited-StateChemistry by Controlling Free Space within aNanocapsule: Photochemistry of 1-(4-Alkylphenyl)-3-phenylpropan-2-onesBy Sundaresan, Arun Kumar, Ramamurthy,V.From Organic Letters, 9(18), 3575-3578;2007
Experimental Procedure2. 1-(Bromomethyl)-4-alkylbenzene (9): To a solution of 8 (1 equivalent) in dichloromethane cooled to -40 °C in a dry ice /acetone bath under nitrogen atmosphere, boron tribromide (1.1 equivalents) wasadded over 15 min and was stirred for 30 min period at 0 °C. The solvent was distilled and the residuewas passed through a silica column eluting with hexane to obtain 9 (colorless liquid). yield 70%. 99 %pure by GC.
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.21. Single Step
90%
Overview
Steps/Stages Notes
1.1 R:CBr4, R:PPh3, S:CH2Cl2Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesDesign and synthesis of phenethylbenzo[1,4]oxazine-3-ones as potent inhibitorsof PI3KinaseγBy Lanni, Thomas B. et alFrom Bioorganic & Medicinal ChemistryLetters, 17(3), 756-760; 2007
SciFinder® Page 12
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.22. Single Step
95%
Overview
Steps/Stages Notes
1.1 R:
R:Br2,
S:CH2Cl2, rt
1.2 R:Na2S2O3, rt
1) NBS can be used instead of Br2, alternativereaction conditions shown, Reactants: 1,Reagents: 3, Solvents: 1, Steps: 1, Stages: 2,Most stages in any one step: 2
References4-Aminophenyldiphenylphosphinite (APDPP),a new heterogeneous and acid scavengerphosphinite - Conversion of alcohols,trimethylsilyl, and tetrahydropyranyl ethers toalkyl halides with halogens or N-halosuccinimidesBy Firouzabadi, Habib et alFrom Canadian Journal of Chemistry, 84(7),1006-1012; 2006
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.23. Single Step
100%
Overview
Steps/Stages Notes
SciFinder® Page 13
1.1 R:Br2, S:908227-64-5, rt1.2 R: 0.5 h, 80°C; 80°C → rt
Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 2, Most stages in any one step: 2
ReferencesA new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highlyselective bromination, thiocyanation, orisothiocyanation of alcohols and trimethylsilyland tetrahydropyranyl ethersBy Iranpoor, Nasser et alFrom Tetrahedron Letters, 47(31), 5531-5534; 2006
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.24. Single Step
100%
Overview
Steps/Stages Notes
1.1 R:Br2, S:908227-64-5, rt1.2 R: 1 h, 80°C; 80°C → rt
Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 2, Most stages in any one step: 2
ReferencesA new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highlyselective bromination, thiocyanation, orisothiocyanation of alcohols and trimethylsilyland tetrahydropyranyl ethersBy Iranpoor, Nasser et alFrom Tetrahedron Letters, 47(31), 5531-5534; 2006
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.25. Single Step
100%
Overview
SciFinder® Page 14
Steps/Stages Notes
1.1 R:Br2, S:908227-64-5, rt1.2 R: 80°C; 80°C → rt
Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 2, Most stages in any one step: 2
ReferencesA new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highlyselective bromination, thiocyanation, orisothiocyanation of alcohols and trimethylsilyland tetrahydropyranyl ethersBy Iranpoor, Nasser et alFrom Tetrahedron Letters, 47(31), 5531-5534; 2006
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.26. Single Step
100%
Overview
Steps/Stages Notes
1.1 R:Br2, S:908227-64-5, rt1.2 R: 80°C; 80°C → rt
Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 2, Most stages in any one step: 2
ReferencesA new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highlyselective bromination, thiocyanation, orisothiocyanation of alcohols and trimethylsilyland tetrahydropyranyl ethersBy Iranpoor, Nasser et alFrom Tetrahedron Letters, 47(31), 5531-5534; 2006
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.27. Single Step
95%
SciFinder® Page 15
Overview
Steps/Stages Notes
1.1 R:Br2, S:908227-64-5, rt
1.2 80°C; 80°C → rt
Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 2, Most stages in any one step: 2
ReferencesA new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highlyselective bromination, thiocyanation, orisothiocyanation of alcohols and trimethylsilyland tetrahydropyranyl ethersBy Iranpoor, Nasser et alFrom Tetrahedron Letters, 47(31), 5531-5534; 2006
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.28. Single Step
90%
Overview
Steps/Stages Notes
1.1 R:
R:PPh3,
S:CH2Cl2, rt Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesFacile conversion of alcohols into theirbromides and iodides by N-bromo- and N-iodosaccharins/triphenylphosphine underneutral conditionsBy Firouzabadi, Habib et alFrom Tetrahedron Letters, 47(11), 1771-1775; 2006
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.29. Single Step
89%
SciFinder® Page 16
Overview
Steps/Stages Notes
1.1 R:PBr3 R: rt
1.2 S:CHCl3, rt
1.3 R:K2CO3, S:H2O, 24 h, rt
1) in the dark, quadraphasic phase-vanishingmethod used, Reactants: 1, Reagents: 3,Solvents: 2, Steps: 1, Stages: 3, Most stagesin any one step: 3
ReferencesQuadraphasic phase-vanishing method.Application to bromination reactions thatproduce acidic by-productsBy Rahman, Md. Taifur et alFrom Synlett, (17), 2664-2666; 2005
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.30. Single Step
97%
Overview
Steps/Stages Notes
1.1 R:PCl3 (react with silica gel to obtain silphos), rt; 30 min, rt
1.2 R:Br2, S:MeCN, rt; rt → reflux; 5 min, reflux
1) in-situ generated agent, silica gel used inthe first stage, Reactants: 1, Reagents: 2,Solvents: 1, Steps: 1, Stages: 2, Most stagesin any one step: 2
ReferencesSilicaphosphine (Silphos): a filterable reagentfor the conversion of alcohols and thiols toalkyl bromides and iodidesBy Iranpoor, Nasser et alFrom Tetrahedron, 61(23), 5699-5704; 2005
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.31. Single Step
SciFinder® Page 17
100%
Overview
Steps/Stages Notes
1.1 R:PCl3 (react with silica gel to obtain silphos), rt; 30 min, rt
1.2 R:Br2, S:MeCN, rt; rt → reflux; 5 min, reflux
1) in-situ generated agent, optimization study,optimized on molar ratio of bromine andsilicagel, silica gel used in the first stage,Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 2, Most stages in any one step: 2
ReferencesSilicaphosphine (Silphos): a filterable reagentfor the conversion of alcohols and thiols toalkyl bromides and iodidesBy Iranpoor, Nasser et alFrom Tetrahedron, 61(23), 5699-5704; 2005
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.32. Single Step
100%
Overview
Steps/Stages Notes
1.1 R:PCl3 (react with silica gel to obtain silphos), rt; 30 min, rt
1.2 R:Br2, S:MeCN, rt; rt → reflux; 5 min, reflux
1) in-situ generated agent, optimization study,optimized on temperature of the first stage,silica gel used in the first stage, Reactants: 1,Reagents: 2, Solvents: 1, Steps: 1, Stages: 2,Most stages in any one step: 2
ReferencesSilicaphosphine (Silphos): a filterable reagentfor the conversion of alcohols and thiols toalkyl bromides and iodidesBy Iranpoor, Nasser et alFrom Tetrahedron, 61(23), 5699-5704; 2005
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.
SciFinder® Page 18
33. Single Step
100%
Overview
Steps/Stages Notes
1.1 R:P(OEt)3, rt; rt → 110°C; 144 h, 110°C
1.2 R:Br2, S:MeCN, rt; rt → reflux; 0.33 h, reflux
1) in-situ generated agent, optimization study,optimized on supporting bed,molar ratio ofreagents,reaction time, silica gel used in firststage, Reactants: 1, Reagents: 2, Solvents: 1,Steps: 1, Stages: 2, Most stages in any onestep: 2
ReferencesSilicaphosphine (Silphos): a filterable reagentfor the conversion of alcohols and thiols toalkyl bromides and iodidesBy Iranpoor, Nasser et alFrom Tetrahedron, 61(23), 5699-5704; 2005
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.34. Single Step
99%
Overview
Steps/Stages Notes
1.1 R:SOCl2, C:1H-Benzotriazole, S:CH2Cl2, 5 min
1.2 R:KBr, S:DMF, 30 min
Reactants: 1, Reagents: 2, Catalysts: 1,Solvents: 2, Steps: 1, Stages: 2, Most stagesin any one step: 2
ReferencesEfficient and selective halogenation of allylicand benzylic alcohols under mild conditionsBy Bandgar, Babasaheb P., Bettigeri,Sampada V.From Monatshefte fuer Chemie, 135(10),1251-1255; 2004
SciFinder® Page 19
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.35. Single Step
93%
Overview
Steps/Stages Notes
1.1 R:t-BuBr R:
,
S:343851-31-0, 0.8 h 1) green chemistry-reagent, ultrasound, ionicliquid may be recycled, alternate preparationsdescribed, Reactants: 1, Reagents: 2,Solvents: 1, Steps: 1, Stages: 1, Most stagesin any one step: 1
ReferencesDirect halogenation of alcohols and theirderivatives with tert-Butyl halides in the ionicliquid [pmIm]Br under sonication conditions -a novel, efficient and green methodologyBy Ranu, Brindaban C., Jana, RanjanFrom European Journal of OrganicChemistry, (4), 755-758; 2005
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.36. Single Step
98%
Overview
Steps/Stages Notes
SciFinder® Page 20
1.1 C:85100-78-3, S:85100-78-3, 15 h, 90°C Reactants: 1, Catalysts: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesMethod for converting primary alcohol orcyclohexanol into alkyl halide in acidic ionliquid [Hmin]+X- (X = Cl, Br, I)By Tang, Jie et alFrom Faming Zhuanli Shenqing GongkaiShuomingshu, 1440958, 10 Sep 2003
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.37. Single Step
99%
Overview
Steps/Stages Notes
1.1 R:
,
S:101023-58-9, 12 h, 120°C 1) Other product also detected, The reagentitself acts as catalyst which can be recycledand reused, Green chemistry-catalyst, reagentand solvent, Reactants: 1, Reagents: 1,Solvents: 1, Steps: 1, Stages: 1, Most stagesin any one step: 1
ReferencesImmobilization of HX. [Hmim]X ashalogenating agent, recyclable catalyst, andmedium for conversion of alcohols to alkylhalidesBy Wu, Hai-Hong et alFrom Chinese Journal of Chemistry, 22(7),619-621; 2004
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.38. 2 Steps
SciFinder® Page 21
Overview
Steps/Stages Notes
1.1 R:MeSO3H, S:THF, 2 d, 25°C
1.2 R:NaOBr, R:LiBr, S:H2O, S:EtCH2Et, S:DMSO, rt; 30 min, < 20°C
2.1 S:CDCl3, 1 h, rt
2) photochemical, addition of H-donorschanges product distribution, Reactants: 2,Reagents: 3, Solvents: 5, Steps: 2, Stages: 3,Most stages in any one step: 2
ReferencesArylmethyl radicals fromarylmethoxybromodiazirinesBy Moss, Robert A., Fu, XiaolinFrom Organic Letters, 6(19), 3353-3356;2004
Experimental ProcedureStep 1General/Typical Procedure: A mixture of 2-naphthylmethanol (10.0 g, 63.2 mmol), cyanamide (2.66g,63.2 mmol), methanesulfonic acid (4.10 mL, 63.2 mmol), and 10.0 mL of dry THF was stirred for 2 dat 25°C in a 100 mL round bottom flask protected with a CaCl2 tube. The reaction mixture was pouredinto 100 mL of ether and chilled in the refrigerator. To a mixture of 4.2 g of lithium bromide in 100 mLof DMSO was added 1.0 g of the above isouronium salt and 100 mL of pentane. The mixture wascooled and maintained below 20°C. Then 100 mL of an aqueous sodium hypobromite solution wasadded dropwise with stirring over 30 min. [The NaOBr solution was prepared by dropwise addition of7.0 mL of bromine to a cold (-5°C) solution of 40 g of sodium bromide and 13.0 g of sodium hydroxidein 100 mL of water.] The reaction mixture was then transferred to a separatory funnel and the aqueouslayer drained. The pentane phase was washed with cold brine and then dried over CaCl2 The pentanesolution was then concentrated to ~10 mL on the rotary evaporator and chromatographed over silicagel with pentane eluent. 3-Benzyloxy-3-bromodiazirine. UV (λmax, pentane) 348 nm. 1H NMR (δ,CDCl3): 7.40-7.28 (m, 5H, phenyl), 4.88 (s, 2H, CH2). 13C NMR (δ, CDCl3): 134.1, 128.8, 128.7,128.4. 70.6, 60.0.
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.39. Single Step
SciFinder® Page 22
88%
Overview
Steps/Stages Notes
1.1 R:Bromosuccinimide, R:PPh3, 10 s 1) green chemistry, microwave irradiation, nosolvent, Reactants: 1, Reagents: 2, Steps: 1,Stages: 1, Most stages in any one step: 1
ReferencesAn efficient and fast method for thepreparation of benzylic bromidesBy Lee, Jong Chan, Hwang, Eui YongFrom Synthetic Communications, 34(16),2959-2963; 2004
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.40. Single Step
68%
Overview
Steps/Stages Notes
1.1 R:
R:p-MeC6H4SO3H,
S:PhMe, 3 min, 200°C, 200 Pa 1) microwave irradn., thermal, high pressure,Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesIonic liquids as reagents and solvents inconjunction with microwave heating: rapidsynthesis of alkyl halides from alcohols andnitriles from aryl halidesBy Leadbeater, Nicholas E. et alFrom Tetrahedron, 59(13), 2253-2258; 2003
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.
SciFinder® Page 23
41. Single Step
97%
Overview
Steps/Stages Notes
1.1 R:SOBr2, S:355-42-0, S:PhMe, 14 h, rt 1) yield depends on reaction conditions,Reactants: 1, Reagents: 1, Solvents: 2, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesFluorous Solvent as a New Phase-ScreenMedium between Reagents and Reactants inthe Bromination and Chlorination of AlcoholsBy Nakamura, Hiroyuki et alFrom Organic Letters, 5(8), 1167-1169; 2003
Experimental ProcedureGeneral/Typical Procedure: General Procedure for Phase-Vanishing Bromination of Alcohols usingSOBr 2 (Table 1, entry 1). FC-72 (perfluorohexane, 2 mL) was placed in a test tube and thionyl bromide(0.12 mL, 1.5 mmol) was introduced slowly by using a glass pipette. The heavier thionyl bromide (d =2.68) sank to the bottom, forming two layers. The slow addition of benzyl alcohol 1a (54 mg, 0.5 mmol)dissolved in toluene (2 mL) formed a triphasic system. The reaction progress in the upper toluene layerwas monitored by GC analysis. Benzyl alcohol 1a was consumed for 14 h and the toluene layer wasdecanted, washed with water, dried over anhydrous MgSO4 , and then concentrated. Purification byshort column chromatography on silica gel with hexane. Compound no 2a.14 hours, benzyl bromide 2ain 97% yield (83 mg, 0.49 mmol).
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.42. Single Step
70%
Overview
Steps/Stages Notes
SciFinder® Page 24
1.1 R:Bu4N+•Br-, R:DDQ, R:PPh3, S:CH2Cl2, rtReactants: 1, Reagents: 3, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesTriphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone as a new, selective andneutral system for the facile conversion ofalcohols, thiols and selenols to alkyl halides inthe presence of halide ionsBy Iranpoor, N. et alFrom Tetrahedron, 58(43), 8689-8693; 2002
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.43. Single Step
98%
Overview
Steps/Stages Notes
1.1 R:Cyanurictrichloride, R:NaBr, R:DMF, S:CH2Cl21) chemoselective, Reactants: 1, Reagents: 3,Solvents: 1, Steps: 1, Stages: 1, Most stagesin any one step: 1
ReferencesAn Efficient Route to Alkyl Chlorides fromAlcohols Using the Complex TCT/DMFBy De Luca, Lidia et alFrom Organic Letters, 4(4), 553-555; 2002
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.44. Single Step
98%
Overview
Steps/Stages Notes
SciFinder® Page 25
1.1 R:Et3SiH, R:PdCl2Reactants: 2, Reagents: 2, Steps: 1, Stages:2, Most stages in any one step: 2
ReferencesThe versatile behavior of the PdCl2/Et3SiHsystem. Conversion of alcohols to thecorresponding halides and alkanesBy Ferreri, C. et alFrom Journal of Organometallic Chemistry,554(2), 135-137; 1998
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.45. Single Step
94%
Overview
Steps/Stages Notes
1.1 R:CBr4, C:Cu, C:Fe, C:CuBr, C:1,10-Phenanthroline, S:DMF
1.2 R:HCl, S:H2O
1) catalyst formed in-situ, other solvents givelower yields, Reactants: 1, Reagents: 2,Catalysts: 4, Solvents: 2, Steps: 1, Stages: 2,Most stages in any one step: 2
ReferencesA New Preparative Route to Organic Halidesfrom Alcohols via the Reduction ofPolyhalomethanesBy Leonel, E. et alFrom Journal of Organic Chemistry, 62(20),7061-7064; 1997
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.46. Single Step
95%
Overview
Steps/Stages Notes
SciFinder® Page 26
1.1 R:NaBr 1) microwave, NaBr doped on K-10 clay,Reactants: 1, Reagents: 1, Steps: 1, Stages:1, Most stages in any one step: 1
ReferencesSelective preparation of benzylic bromides indry media coupled with microwave irradiationBy Kad, Goverdhan L. et alFrom Tetrahedron Letters, 38(6), 1079-1080;1997
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.47. Single Step
81%
Overview
Steps/Stages Notes
1.1 R:Bromosuccinimide, R:PPh3, S:Dioxane Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesFormation of acyl bromides from carboxylicacids and N-bromosuccinimide; somereactions ofbromocyanotriphenylphosphoraneBy Fryeyen, PaulFrom Phosphorus, Sulfur and Silicon and theRelated Elements, 102(1-4), 253-9; 1995
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.48. 2 Steps
Overview
Steps/Stages Notes
SciFinder® Page 27
1.1 R:SnCl42.1 R:BBr3
Reactants: 1, Reagents: 2, Steps: 2, Stages:2, Most stages in any one step: 1
ReferencesA simple method for the conversion ofadamantyl, benzyl and benzyhydryl alcoholsto their corresponding bromides and chloridesand the transhalogenation of adamantyl,benzyl, benzhydryl and tertiary alkyl bromidesand chloridesBy Amrollah-Madjdabadi, A. et alFrom Synthesis, (8), 614-16; 1989
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.49. Single Step
93%
Overview
Steps/Stages Notes
1.1 R:BBr3Reactants: 1, Reagents: 1, Steps: 1, Stages:1, Most stages in any one step: 1
ReferencesA simple method for the conversion ofadamantyl, benzyl and benzyhydryl alcoholsto their corresponding bromides and chloridesand the transhalogenation of adamantyl,benzyl, benzhydryl and tertiary alkyl bromidesand chloridesBy Amrollah-Madjdabadi, A. et alFrom Synthesis, (8), 614-16; 1989
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.50. Single Step
87%
Overview
SciFinder® Page 28
Steps/Stages Notes
1.1 R:PBr3, S:Et2OReactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesEffect of structure factors on the rate ofbimolecular homolytic substitution at carbonin benzylcobalt complexesBy Dneprovskii, A. S. et alFrom Zhurnal Organicheskoi Khimii, 24(5),923-9; 1988
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.51. Single Step
80%
Overview
Steps/Stages Notes
Reactants: 1, Steps: 1, Stages: 1, Most stagesin any one step: 1
ReferencesCollision-induced dissociations of aryl-substituted alkoxide ions. Losses ofdihydrogen and rearrangement processesBy Raftery, Mark J. et alFrom Journal of the Chemical Society, PerkinTransactions 2: Physical Organic Chemistry(1972-1999), (4), 563-9; 1988
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.52. Single Step
88%
SciFinder® Page 29
Overview
Steps/Stages Notes
1.1 R:Triflicacid, R:Bu4N+•Br-, S:CH2Cl2Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesConversion of alcohols into alkyl bromidesand iodides via O-alkylisoureasBy Collingwood, Stephen P. et alFrom Tetrahedron Letters, 28(38), 4445-8;1987
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.53. Single Step
100%
Overview
Steps/Stages Notes
1.1 R:PBr3, S:ClCH2CH2Cl Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesPrimary and secondary kinetic deuteriumisotope effects and transition-state structuresfor benzylic chlorination and bromination oftolueneBy Hanzlik, Robert P. et alFrom Journal of the American ChemicalSociety, 109(16), 4926-30; 1987
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.54. Single Step
SciFinder® Page 30
Overview
Steps/Stages Notes
1.1 R:
R:BF3-Et2O,
S:CHCl3 Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesBoron trifluoride etherate/halide ion, a novelreagent for the conversion of allyl, benzyl andtertiary alcohols to the halidesBy Mandal, Arun K., Mahajan, S. W.From Tetrahedron Letters, 26(32), 3863-6;1985
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.55. Single Step
Overview
Steps/Stages Notes
1.1 R:HBr, S:H2OReactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesAromatic rearrangements in the benzeneseries. Part 4. Intramolecularity of both theortho- and para-rearrangements of benzylphenyl ether as shown by labelingexperimentsBy Hart, Lionel S., Waddington, Catherine R.From Journal of the Chemical Society, PerkinTransactions 2: Physical Organic Chemistry(1972-1999), (10), 1607-12; 1985
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.56. Single Step
SciFinder® Page 31
Overview
Steps/Stages Notes
1.1 R:EtO2CN=NCO2Et, R:PPh3, R:LiBr, S:THF Reactants: 1, Reagents: 3, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesA convenient preparation of alkyl halides andcyanides from alcohols by modification of theMitsunobu procedureBy Manna, Sukumar et alFrom Synthetic Communications, 15(8), 663-8; 1985
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.57. Single Step
Overview
Steps/Stages Notes
1.1 R:HBr, S:Benzene Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesIntramolecular kinetic deuterium isotopeeffects on microsomal hydroxylation andchemical chlorination of toluene-α-d1 andtoluene-α,α-d2By Hanzlik, Robert P. et alFrom Journal of the American ChemicalSociety, 107(24), 7164-7; 1985
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.
SciFinder® Page 32
58. Single Step
Overview
Steps/Stages Notes
1.1 R:HBr, S:Benzene Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesIntramolecular kinetic deuterium isotopeeffects on microsomal hydroxylation andchemical chlorination of toluene-α-d1 andtoluene-α,α-d2By Hanzlik, Robert P. et alFrom Journal of the American ChemicalSociety, 107(24), 7164-7; 1985
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.59. Single Step
80%
Overview
Steps/Stages Notes
Reactants: 2, Steps: 1, Stages: 1, Most stagesin any one step: 1
ReferencesConversion of alcohols into alkyl bromidesusing polymer-supported triphenylphosphinedibromide and polymer-supportedtriphenylphosphine and carbon tetrabromideBy Hodge, Philip, Khoshdel, EzzatollahFrom Journal of the Chemical Society, PerkinTransactions 1: Organic and Bio-OrganicChemistry (1972-1999), (2), 195-8; 1984
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CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.60. Single Step
82%
Overview
Steps/Stages Notes
1.1 R:PBr3 (polymer-bound) Reactants: 1, Reagents: 1, Steps: 1, Stages:1, Most stages in any one step: 1
ReferencesPolymer-bonded Lewis acids in organicsynthesis: conversion of carboxylic acids intoacyl chlorides and of alcohols into alkylchlorides or bromides by polymer-bondedphosphorus reagentsBy Cainelli, Gianfranco et alFrom Synthesis, (4), 306-8; 1983
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.61. Single Step
100%
Overview
Steps/Stages Notes
1.1 R:Me3SiCl, S:MeCN 1) Classification: Substitution; Bromination; #Conditions: Me3SiCl + LiBr; MeCN; Rf / N2,Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesChlorotrimethylsilane/lithium bromide andhexamethyldisilane/pyridinium bromideperbromide: effective and selective reagentsfor the conversion of alkyl (cycloalkyl andaralkyl) alcohols into bromidesBy Olah, George A. et alFrom Journal of Organic Chemistry, 45(9),1638-9; 1980
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CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.62. Single Step
100%
Overview
Steps/Stages Notes
1.1 R:Py•HBr3, R:(Me3Si)2NH, S:CHCl31) Classification: Substitution; Bromination; #Conditions: py.HBr3; HMDS; CHCl3 dry;30mn; # Comments: reference Synthesis(1981) p325; yield in range 78% to 100%,Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesChlorotrimethylsilane/lithium bromide andhexamethyldisilane/pyridinium bromideperbromide: effective and selective reagentsfor the conversion of alkyl (cycloalkyl andaralkyl) alcohols into bromidesBy Olah, George A. et alFrom Journal of Organic Chemistry, 45(9),1638-9; 1980
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.63. Single Step
Overview
Steps/Stages Notes
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1.1 R:NH4Br, C:HF-pyridine Reactants: 1, Reagents: 1, Catalysts: 1, Steps:1, Stages: 1, Most stages in any one step: 1
ReferencesSynthetic methods and reactions. 63.Pyridinium poly(hydrogen fluoride) (30%pyridine-70% hydrogen fluoride): aconvenient reagent for organic fluorinationreactionsBy Olah, George A. et alFrom Journal of Organic Chemistry, 44(22),3872-81; 1979
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.64. Single Step
Overview
Steps/Stages Notes
1.1 R:HBr Reactants: 1, Reagents: 1, Steps: 1, Stages:1, Most stages in any one step: 1
ReferencesSynthesis of 14C-methyl benzyl nitrosamineand methyl 14C-benzyl nitrosamineBy Skipper, Paul L.From Journal of Labelled Compounds andRadiopharmaceuticals, 15(Suppl. Vol.), 575-9; 1978
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.65. Single Step
80% (80:20 ) 80% (80:20 )
Overview
Steps/Stages Notes
SciFinder® Page 36
1.1 R:CBrCl3, C:Cu, C:Fe, C:CuBr, C:1,10-Phenanthroline, S:DMF
1.2 R:HCl, S:H2O
1) catalyst formed in-situ, other solvents givelower yields, Reactants: 1, Reagents: 2,Catalysts: 4, Solvents: 2, Steps: 1, Stages: 2,Most stages in any one step: 2
ReferencesA New Preparative Route to Organic Halidesfrom Alcohols via the Reduction ofPolyhalomethanesBy Leonel, E. et alFrom Journal of Organic Chemistry, 62(20),7061-7064; 1997
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.
SciFinder® Page 37