4-Bromo-2-fluorobenzaldehyde → (4-Bromo-2-fluorophenyl)methanol

Participants

Reaction Steps

To a stirred solution of 4-Bromo-2-fluoro benzaldehyde (15 g, 79.36 mmol) in MeOH (100 mL) at −5° C. to 0° C. was added NaBH4 (6.0 g, 158.73 mmol) in equal portions and stirred at RT for 1 h until the starting material was completely consumed, as evidenced by TLC analysis. The reaction mixture was then diluted with ice cold water (100 mL) and concentrated under reduced pressure. The residue obtained on concentration was extracted with EtOAc (2×200 mL) and separated. The combined EtOAc layers were washed with brine solution (50 mL), dried over anhydrous NaSO4, filtered and concentrated to afford (4-bromo-2-fluorophenyl)methanol (30 g, 99% (from 2 batches))] as colorless oil (TLC solvent system: 30% EtOAc in PE; Rf: 0.3).

Provenance & Evidence