Triethylamine → 3-Bromo-4-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

3-Bromo-4-methylbenzoic acid (1.5 g, 7.0 mmol) in thionyl chloride (10 mL) was heated to 80° C. for 1 h. The solvent was removed in vacuo and the residue was dissolved in DCM (16 mL) at 0° C. under argon before adding ammonium chloride (410 mg, 7.7 mmol) and Et3N (2.43 mL, 17.4 mmol). The reaction was stirred at 0° C. for 15 min then allowed to warm to rt over 16 h. The solvent was removed in vacuo and the mixture partitioned between EtOAc (120 mL) and 1M NaOH (60 mL). The organic phase was washed with 1M NaOH (60 mL), brine (60 mL) and dried (MgSO4). The solvent was removed in vacuo. Trituration with ether and then MeOH gave the title compound: RT=2.78 min; m/z (ES+)=214.0 [M+H]+.

Provenance & Evidence