Boron tribromide → 2-Chloro-4-hydroxybenzenebutanoic acid

Participants

Reaction Steps

To a solution of tert-butyl 4-(2-chloro-4-methoxyphenyl)butanoate (1.73 g) in dichloromethane (10.0 mL) were added under ice-cooling, and a 1 M solution of boron tribromide in dichloromethane (12.2 mL), followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure and basified by the addition of a saturated aqueous sodium hydrogen carbonate solution, and 1 M hydrochloric acid was added thereto until the liquid became acidic. The precipitated insoluble material was collected by filtration and dried under reduced pressure to obtain 4-(2-chloro-4-hydroxyphenyl)butanoic acid (647 mg).

Provenance & Evidence