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

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Reaction Steps

To a solution 5-bromo-2-chlorobenzoic acid (compound 3, 100 g, 425 mmol) in tetrahydrofuran (500 mL) at 0° C. 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 methanol. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo to yield the title compound as a white solid, which was used without further purification.

Provenance & Evidence