Borane;tetrahydrofuran → 3-(4-Bromophenyl)propan-1-ol

Participants

Reaction Steps

To a stirred solution of 3-(4-bromophenyl)propanoic acid (7 g, 30.56 mmol) in THF (50.9 ml) at −10° C. was added borane tetrahydrofuran complex (1M in THF) (153 ml, 152.79 mmol) dropwise over 1 h, keeping the temperature below 0° C. The reaction mixture was allowed to warm to RT overnight then cooled to 5° C. and quenched with MeOH (50 mL). Reaction mixture stirred at RT for 1 h and then concentrated to give an oil. The oil was partitioned between ether (120 mL) and 2M NaOH (60 mL). The organic layer was then washed with water (60 mL) and brine, dried over magnesium sulfate, filtered and evaporated to afford the sub-title compound. Yield: 6.17 g

Provenance & Evidence