Sodium Carbonate → (3-Bromo-5-fluorophenyl)methanol

Participants

Reaction Steps

BH3.THF in THF (1.00 M, 4.44 ml) was added dropwise into the THF (10 ml) solution of 3-bromo-5-fluorobenzoic acid (447 mg, 2.00 mmol) at rt under an atmosphere of nitrogen. The combined solution was stirred at rt for 24 h. After that time, the mixture was diluted with EtOAc (50 ml) and treated with saturated Na2CO3 (30 ml). The aqueous layer was extracted with EtOAc (2×25 ml). The extracts were washed with water (3×30 ml), brine (30 ml), dried over MgSO4, filtered and concentrated in vacuo to give the title compounds as colorless oil. 1H NMR (400 MHz, CDCl3): δ=1.83 (brs, 1H), 4.71 (s, 2H), 7.03-7.08 (m, 1H), 7.16-7.20 (m, 1H), 7.32-7.34 (m, 1H). HPLC: tR=2.87 min (polar—5 min, ZQ3).

Provenance & Evidence