Hydrogen Bromide → alpha-Bromo-o-chlorotoluene

HRID 1291134Notes

Reaction equation

HRID 1291134 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]O.[BrH:10]>>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][Br:10]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 288102-Chlorobenzyl alcohol

Product 1

HCID 11905alpha-Bromo-o-chlorotolueneYield 85%

Procedure

100 ml of HBr (48%) were heated to 90° and treated portionwise with 1.43 g (0.01 mol) of 2-chlorobenzyl alcohol. The mixture was stirred for 1/4 hr. and then cooled to room temperature. The mixture was extracted with ethyl acetate and the organic phase was washed with water and saturated sodium chloride solution and dried over sodium sulfate. 1.75g (85%) of 2-chlorobenzyl bromide were obtained as a slightly turbid, colorless oil; b.p. 130°/30 mmHg.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic phase was washed with water and saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-c2418d803a574f2ca905dc5d804a7f5a
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

Loading…