(4-Chlorophenyl)acetic acid → alpha-Bromo-4-chlorophenylacetic acid

Participants

Reaction Conditions

Reaction Steps

80.0 g (469 mmol) of 4-chlorophenylacetic acid are dissolved in 200 ml of tetrachloroethane under argon and heated under RF. While boiling, 100 g (563 mmol) of N-bromosuccinimide and 7.70 g (46.9 mmol) of 2,2′-azobis-2-methylpropanenitrile are added, and the mixture is heated under RF overnight. It is then cooled to 0° C. and filtered with suction, the precipitate is washed with cold tetrachloromethane, and the filtrate is concentrated. The residue is dissolved in diethyl ether and extracted three times with saturated aqueous bicarbonate solution. The combined aqueous phases are adjusted to a pH of 1 with concentrated hydrochloric acid and extracted four times with diethyl ether. The combined organic phases are dried over magnesium sulfate, filtered and concentrated to result in 83.0 g (71% of theory) of the product, which is reacted further without further purification.

Provenance & Evidence