4-(Bromomethyl)phenylacetic acid → 2-[4-(Aminomethyl)phenyl]ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of NH3/EtOH (170 mL) was added (4-Bromomethyl-phenyl)-acetic acid (1.61 g, 7.01 mmol). The resultant solution was stirred at room temperature for 2 h. The mixture was concentrated in vacuo, and redissolved with anhydrous THF (10 mL). To the solution, BH3.Me2S was added, and the mixture was stirred for 1 h at 70° C., and at room temperature for 2 d. The reaction was concentrated in vacuo, 6 N HCl (10 mL) was added, and the mixture was stirred at 70° C. for 1 h. Water (20 mL) was added, and it was neutralized with 1 N NaOH to pH˜7. The solution was concentrated to dryness under high vacuum, washed with MeOH/CH2Cl2, and filtered. The crude product was purified by flash chromatography on silica gel (5:3:92 CH3OH—NH3 H2O—CH2Cl2) to afford the title compound (820 mg, 77%) as a white foam.

Provenance & Evidence