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), stirred overnight at room temperature, treated with an additional 130 mL 1.0 M BH3.THF, stirred 10 hours, quenched by the addition of methanol, stirred 3 hours at room temperature, solvent evaporated, the product partitioned between aqueous sodium bicarbonate/methylene chloride, the organic layer dried (sodium sulfate), filtered and solvent evaporated. The 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