Dimethylformamide → 3-Bromo-4-methylbenzamide

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To a slurry of 3-bromo-4-methylbenzoic acid (2.53 g, 85% purity; 10 mmol) in CH2Cl2 (20 mL) at 0° C., under N2, was added oxalyl chloride (0.91 mL; 10.5 mmol), followed by dropwise addition of DMF (0.04 mL; 0.5 mmol). The mixture was stirred 5 min at 0° C., 15 min at rt, and then heated at reflux under N2 for 1 h. The mixture was cooled, and poured into NH4OH (30 mL; ca. 30% NH3). Precipitated solids were collected by filtration and purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless solid. LC/MS (method A) tR 2.05 min; m/z 214, 216 (M+H, Br isotopes).

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