Dimethylformamide → HCID 53417502, compound

Participants

Reaction Steps

To a solution of 3-bromo-5-(trifluoromethyl)benzoic acid (50 g, 186 mmol) in DCM (500 mL) at 0° C., was added Oxalyl chloride (30.7 g, 242 mmol) with catalytical amount of DMF (0.5 mL). After stirring for 30 min the reaction mixture was concentrated. To a suspension of N,O-dimethylhydroxylamine hydrochloride (23.5 g, 242 mmol) in DCM (300 mL) at 0° C. was added TEA (51 g, 500 mol). Then a solution of acid chloride in DCM (300 mL) was added slowly. After stirring for 1 h, the reaction mixture was poured into water (200 mL) with vigorous stirring, extracted with DCM (2×200 mL). The organic layers were washed with brine (50 mL), dried over anhydrous MgSO4 and then concentrated. The residue was purified by silica gel chromatography (PE/EtOAc=20/1 to 5/1) to give the title compound (47 g, yield: 81%); m/z (ES+): 312 [M+H]+.

Provenance & Evidence