3-Bromo-2-fluorobenzoic acid → 3-Bromo-2-fluorobenzyl Alcohol

Participants

Reaction Steps

A cooled (0° C.) solution of 3-bromo-2-fluorobenzoic acid (Fluorochem; 500 mg; 2.28 mmol) in anhydrous THF (4 mL) was slowly treated with borane-tetrahydrofuran complex (3.42 mL; 1.00 M; 3.42 mmol) and the resulting solution was stirred at RT for 2 days. Borane-tetrahydrofuran complex (3.42 mL; 1.00 M; 3.42 mmol) was added and the reaction mixture was stirred at RT for a further 3 hours. The reaction was carefully quenched with water and the mixture was concentrated. The residue was dissolved in Et2O, and the aqueous phase was saturated with K2CO3. The organic layer was separated and the aqueous phase was extracted with Et2O. The combined organic phases were washed with water and brine, dried over MgSO4 and concentrated to dryness affording the title compound as a colorless oil.

Provenance & Evidence