Methanol → 2-Bromo-5-fluorobenzyl alcohol

Participants

Reaction Steps

To a solution of methyl 2-bromo-5-fluorobenzoate (10, 21.30 g, 91.4 mmol) in dry THF (150 mL) was added NaBH4 (6.95 g, 183 mmol). Methanol (20 mL) was added dropwise at RT. After the addition, the mixture was stirred at RT for 1 h. Water (200 mL) was slowly added. The mixture was extracted with CH2Cl2 (100 mL×2). The combined extracts were washed with saturated NaHCO3 and brine, dried over MgSO4 and concentrated to give (2-bromo-5-fluorophenyl)methanol (11).

Provenance & Evidence