Benzeneacetic acid, 4-bromo- → 2-(4-Bromophenyl)ethanol

Participants

Reaction Steps

To a chilled solution (about 0° C.) of 4-bromophenyl acetic acid (25 g, 0.116 mol) in THF (250 mL), borane methyl sulphide (13.2 g, 0.174 mol) was added, dropwise, under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 3 h. After cooling the mixture to between 0 and 5° C., the reaction was quenched by adding 1.5 N HCl (80 mL), dropwise. After warming for 30 min at about 80° C., the reaction mixture was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with water and brine and then dried. The product was obtained as colourless liquid after concentration (yield: 23.3 g, 99%).

Provenance & Evidence