5-Bromo-2-chlorobenzoic acid → (5-Bromo-2-chlorophenyl)methanol

Participants

Reaction Steps

To a solution 5-bromo-2-chlorobenzoic acid (100 g, 425 mmol) in tetrahydrofuran (500 mL) at 0 r was added borane dimethyl sulfide complex (170 mL, 170 mmol). The resulting mixture was stirred with gradual warming to ambient temperature over 15 h, re-cooled to 0° C., and quenched with MeOH. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to yield the titiled compound as a white solid, which was used without further purification.

Provenance & Evidence