Bromine → 2-Cyanobenzenesulfenyl bromide

HRID 1292561

Reaction equation

HRID 1292561 reaction equation
C[S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]#[N:10].[Br:11]Br>ClC1C=CC=CC=1>[C:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[S:2][Br:11])#[N:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 1387812-(Methylthio)benzonitrile

Product 1

HCID 153754842-Cyanobenzenesulfenyl bromideYield 84.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

74.5 g (0.500 mol) of 2-cyanophenyl methyl sulfide and 250 g of chlorobenzene were placed in a 500 ml four-neck flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser and 96.0 g (0.600 mol) of bromine was added dropwise thereto at about 100° C. over five hours while stirring. The excess bromine was removed with an aqueous sodium carbonate solution, followed by distillation under reduced pressure to obtain 90.4 g of 2-cyanobenzenesulfenyl bromide. The yield starting from 2-cyanophenyl methyl sulfide was 84.5%.

Workup

  1. customequipped with a stirrer
  2. customThe excess bromine was removed with an aqueous sodium carbonate solution
  3. distillationfollowed by distillation under reduced pressure

Sources & evidence

ORD record
ord-20bf5799bba44e31869a96c3e99008b6
Source dataset
uspto-grants-1998_05
Patent number
US05756806

Linked notes

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