Bromine → Bromo-4-chlorophenylacetyl chloride

HRID 980924Notes

Reaction equation

HRID 980924 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([Cl:13])=[O:12])=[CH:6][CH:5]=1>>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([Br:1])[C:11]([Cl:13])=[O:12])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 24408BromineHCID 906924-Chlorophenylacetyl chloride

Product 1

HCID 12575778Bromo-4-chlorophenylacetyl chlorideYield 85%

Conditions

Temperature
90 °C

Procedure

16 g (0.2 moles) of elemental bromine were added dropwise to 18.9 g (0.1 moles) of 4-chlorophenylacetic acid chloride at 95° C. while stirring. The reaction mixture was maintained for a further 2.5 hours at a temperature of 90° C. and then excess bromine was distilled off. The crude product was finally distilled under 16 mb in a temperature range of from 90° C. to 96° C. 22.9 g (0.085 moles) of 4-chlorophenyl-alpha-bromoacetic acid chloride, corresponding to 85% of the theoretical yield, were obtained.

Workup

  1. distillationexcess bromine was distilled off
  2. distillationThe crude product was finally distilled under 16 mb in a temperature range of from 90° C. to 96° C

Sources & evidence

ORD record
ord-6a970ab3e6f1403b9631cc39af844ade
Source dataset
uspto-grants-1987_01
Patent number
US04639541

Reaction notes

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