S1

Supporting Information

An alternative method for the regio- and stereoselective bromination of

alkenes, alkynes, toluene derivatives and ketones using a

bromide/bromate couple

Subbarayappa Adimurthy,*a Sudip Ghosh,b Paresh U. Patoliya,a Gadde

Ramachandraiah,*a Manoj Agrawal, Mahesh R. Gandhi, Sumesh C. Upadhyay, Pushpito

K. Ghosh,*a Brindaban C. Ranu*b aCentral Salt and Marine Chemicals Research Institute, Gijubhai Badheka Marg, Bhavnagar – 364 002, Gujarat, India. Fax : +91-278-2567562 bDepartment of Organic Chemistry, Indian Association for the Cultivation of Science,

Jadavpur, Kolkata – 700 032, India.

E-mail : sadimurthy@yahoo.com; ocbcr@iacs.res.in; grama@csmcri.org,

pkghosh@csmcri.org

Table of Contents Page no. 1H NMR and 13 C NMR Spectra of All Products S2-S79

in Tables 1-4 and 6

S2

Br

Br

Entry-1, table-1

S3

Br

Br

Entry-1, table-1

S4

PhBr

Br

Entry-2, table-1

S5

PhBr

Br

Entry-2, table-1

S6

Br

Br

Entry-3, table-1

S7

Br

Br

Entry-3, table-1

S8

Br

Br

Entry-4, table-1

S9

Br

Br

Entry-4, table-1

S10

Br

Ph Br

Ph

Entry-5,table-1

S11

Br

Ph Br

Ph

Entry-5,table-1

S12

Br

Ph Br

Ph

Entry-6,table-1

S13

Br

Ph Br

Ph

Entry-6,table-1

S14

Ph

O

COOEt

Br

Br

Entry-7, table-1

S15

Ph

O

COOEt

Br

Br

Entry-7, table-1

S16

Br

COOEt

EtOOC

Br

Entry-8, table-1

S17

Br

COOEt

EtOOC

Br

Entry-8, table-1

S18

Ph

O

Ph

Br

Br

Entry-9, table-1

S19

Ph

O

Ph

Br

Br

Entry-9, table-1

S20

Ph

O

Br

Br

p-OMe ( C6H4)

Entry-10, table-1

S21

Ph

O

Br

Br

p-OMe ( C6H4)

Entry-10, table-1

S22

p-Cl (C6H4)Ph

O

Br

Br

Entry-11, table-1

S23

p-Cl (C6H4)Ph

O

Br

Br

Entry-11, table-1

S24

COPh

Br

Br

PhOC

Entry-12, table-1

S25

COPh

Br

Br

PhOC

Entry-12, table-1

S26

Ph

O

NO2

Br

Br

Entry-13, table-1

S27

Ph

O

NO2

Br

Br

Entry-13, table-1

S28

Br

Br

Entry-1, table-2

S29

Br

Br

Entry-1, table-2

S30

Br

Br

Entry-2, table-2

S31

Br

Br

Entry-2, table-2

S32

Ph

Br

H

Br

Entry-3, table-2

S33

Ph

Br

H

Br

Entry-3, table-2

S34

Br

Br

Entry-4, table-2

S35

Br

Br

Entry-4, table-2

S36

Br

Br

Entry-5, table-2

S37

Br

Br

Entry-5, table-2

S38

Ph

Br

Ph

Entry-6, table-2

Br

S39

Ph

Br

Ph

Entry-6, table-2

Br

S40

MeOOC

Br

Br

COOMe

Entry-7, table-2

S41

MeOOC

Br

Br

COOMe

Entry-7, table-2

S42

Cl

BrBr

H

Entry-8, table-2

S43

Cl

BrBr

H

Entry-8, table-2

S44

BrBr

H

Entry-9, table-2

OMe

S45

BrBr

H

Entry-9, table-2

OMe

S46

BrBr

Br

Entry-10, table-2

H

S47

BrBr

Br

Entry-10, table-2

H

S48

CH3

BrBr

H

Entry-11, table-2

S49

CH3

BrBr

H

Entry-11, table-2

S50

O

Br

Br

Entry-12, table-2

S51

O

Br

Br

Entry-12, table-2

S52

O

Br

Br

Entry-13, table-2

S53

O

Br

Br

Entry-13, table-2

S54

1H-NMR (entry 1, Table 3)

13C-NMR (entry 1, Table 3)

S55

1H-NMR (entry 2, Table 3)

13C-NMR (entry 2, Table 3)

S56

Gas Chromatogram (entry 2, Table 3)

Differential Scanning Calorimeter (DSC) Thermo gram (entry 2, Table 3)

S57

1H-NMR (entry 3, Table 3)

13C-NMR (entry 3, Table 3)

S58

1H-NMR (entry 4, Table 3)

13C-NMR (entry 4, Table 3)

S59

1H-NMR (entry 5, Table 3)

13C-NMR (entry 5, Table 3)

S60

1H-NMR (entry 6, Table 3)

13C-NMR (entry 6, Table 3)

S61

1H-NMR (entry 7, Table 3)

13C-NMR (entry 7, Table 3)

S62

1H-NMR (entry 8, Table 3)

13C-NMR (entry 8, Table 3).

S63

1H-NMR (entry 9, Table 3)

13C-NMR (entry 9, Table 3)

S64

1H-NMR (entry 10, Table 3)

13C-NMR (entry 10, Table 3)

S65

1H-NMR (entry 1, Table 4)

13C-NMR (entry 1, Table 4)

S66

1H-NMR (entry 2, Table 4)

13C-NMR (entry 2, Table 4)

S67

1H-NMR (entry 3, Table 4)

13C-NMR (entry 3, Table 4)

S68

O

Br

Entry-1,table-5

S69

O

Br

Entry-1,table-5

S70

Br

O

Entry-2, table-5

S71

Br

O

Entry-2, table-5

S72

O

Br

Entry-3 ,table-5

S73

O

Br

Entry-3 ,table-5

S74

Br

O

Entry-4,table-5

S75

Br

O

Entry-4,table-5

S76

O

Br

Entry-5 ,table-5

S77

O

Br

Entry-5 ,table-5

S78

O

Br

Entry-6, table-5

S79

O

Br

Entry-6, table-5

S80