3-Amino-4-fluorobenzoic acid → (3-Amino-4-fluorophenyl)methanol

Participants

Reaction Steps

3-Amino-4-fluorobenzoic acid (15 g, 97 mmol) in THF at 0° C. was treated with 1.0 M BH3•THF (50 mL) with stirring overnight at room temperature. An additional 130 mL 1.0 M BH3•THF was added with stirring for 10 hours. The reaction mixture was quenched by the addition of methanol, stirred 3 hours at room temperature, solvent evaporated, and the product partitioned between aqueous sodium bicarbonate/methylene chloride. The organic layer was dried (sodium sulfate), filtered, and the solvent evaporated. The crude product was purified by flash chromatography over silica gel (ethyl acetate/hexane 1:1) to provide 7.0 g of the title compound.

Provenance & Evidence