Nitrogen → 3-(2-Bromophenyl)propan-1-ol

Participants

Reaction Steps

3-(2-Bromophenyl)propionic acid (1.15 g, 5.0 mmol) was placed in a 100 mL three-necked flask with magnetic stirrer. The atmosphere was exchanged with N2 (3 times). With ice cooling, a solution of BH3.THF in THF (1.0M, 7.0 mL, 1.4 equiv.) was added dropwise via syringe with stirring over a 15 min period (H2 evolution). The resulting mixture was stirred in the ice bath for 1 h, and residual borane was quenched by cautious addition of water. The solvents were evaporated, and the residue was partitioned between ether (20 mL) and water (20 mL). The aqueous phase was extracted with ether (20 mL). The combined ether layers were washed with brine, dried over Na2SO4, and concentrated to give the alcohol as a clear oil (1.05 g, 98%). 1H NMR (CDCl3, 400 MHz) δ 7.53 (d, 1H, J=7.8 Hz), 7.26-7.22 (m, 2H), 7.09-7.03 (m, 1H), 3.71 (t, 2H, J=6.4 Hz), 2.87-2.82 (m, 2H), 1.94-1.86 (m, 2H), 1.36 (br s, 1H).

Provenance & Evidence