Bromine → Ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)acetate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl 2-(3-chloro-4-hydroxyphenyl)acetate (15 g, 69 mmol) in CCl4 (270 mL), bromine (11.1 g, 69 mmol) was added slowly (dissolved in 140 mL of CCl4) at −10° C. over a period of 30 min. The reaction mixture was stirred for another 1 h at −10° C. Upon completion of the reaction, the mixture was poured onto crushed ice and extracted with DCM (×2). The combined organic layers were washed with saturated Na2S2O3 solution, water, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude compound was purified by re-crystallization using hexane to yield compound ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)acetate (7 g, 7 g starting material recovered) as a white solid.

Provenance & Evidence