Thionyl Chloride → 2-Bromo-p-chlorophenylacetyl chloride

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.S(Cl)([Cl:15])=O>>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([Cl:15])=[O:12]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 218285032-Bromo-4-chlorophenylacetic acid

Product 1

HCID 197942342-Bromo-p-chlorophenylacetyl chlorideYield 88.2%

Procedure

28.3g (0.113 mol) of 2-bromo-p-chlorophenylacetic acid was mixed with 26.9g (0.226 mol) of thionylchloride and the mixture was refluxed for 2.5 hours. After the excess thionylchloride had been distilled off, the reaction mixture was distilled under reduced pressure to give 26.7g of 2-bromo-p-chlorophenylacetyl chloride as yellow-orange oil. (b.p. 148° - 152°C/15 mmHg)

Workup

temperaturethe mixture was refluxed for 2.5 hours
distillationAfter the excess thionylchloride had been distilled off
distillationthe reaction mixture was distilled under reduced pressure

Sources & evidence

ORD record: ord-0a9b9b78ae254be2987c42d7e132ee20
Source dataset: uspto-grants-1976_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03971828

Reaction notes

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