Methanol → (R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol

Participants

Reaction Steps

A solution of BH3.THF in THF (1 M, 108.00 mL, 108.00 mmol) was added to a solution of 1-(4-benzyloxy-3-nitrophenyl)-2-bromoethanone (3) (63.30 g, 180.00 mmol) and R-methyl-CBS-oxazoborolidine (1 M in toluene, 36.00 mL, 36.00 mmol) in anhydrous THF (500 mL). The resulting reaction mixture was stirred at rt for 16 h. Methanol (250 mL) was then slowly added to quench the reaction. After removal of solvent by rotary evaporation, the resulting residue was purified by column chromatography (silica gel, a gradient of 70:30 to 100:0 dichloromethane/hexanes) to give the desired bromo alcohol 4 as a yellow, viscous oil (36.80 g, 75% yield): 1H NMR (500 MHz, CDCl3) δ 2.72 (d, 1H), 3.48 (dd, 1H), 3.59 (dd, 1H), 4.89 (m, 1H), 5.21 (s, 2H), 7.11 (d, 1H), 7.39 (m, 5H), 7.50 (dd, 1H), 7.87 (d, 1H).

Provenance & Evidence