Ammonia → 3-(2-Bromophenyl)propanamide

Participants

Reaction Steps

To a solution of commercially available 3-(2-bromophenyl)propanoic acid (1 eq.) in CH2Cl2 (0.22M) at room temperature was added oxalyl chloride (16 eq) and a catalytic amount of DMF. The mixture was stiffed for 2 h, diluted with toluene (0.022M) and concentrated. To the residue diluted in CH2Cl2 (0.1M) at 0° C. was added ammonia (0.5M in dioxanne (3 eq.). The mixture was stiffed 2 h at room temperature, concentrated, quenched with aqueous NaOH 1N and then extracted with EtOAc. The organic extract was washed with water, brine, dried over MgSO4 filtered and concentrated. Recrystallization in Et2O/hexane (1:1) afforded the desired compound as a white solid.

Provenance & Evidence