4-Fluorobenzoic Acid → N-[(dimethylamino)sulfonyl]-4-fluorobenzamide

Participants

Reaction Steps

To a solution of 4-fluorobenzoic acid (700 mg, 5.0 mmol) in 1,2-dichloroethane (30 mL) was added EDCI (2.38 g, 12.5 mmol), DMAP (1.52 mg, 12.5 mmol) and N,N-diisopropylethylamine (2.17 mL, 12.5 mmol) and stirred for 20 minutes at room temperature. N,N-dimethylaminosulfonamide (1.24 g, 10.0 mmol) was added to the solution and the mixture heated at 60° C. for 2.5 hours. The mixture was cooled, diluted with water (20 mL) and 2M HCl (20 mL) and extracted with DCM (3×30 mL), washed with water (20 mL) and dried over MgSO4. The solvent was removed in vacuo to afford the title compound as a white solid (585 mg, 47%). No further purification was necessary.

Provenance & Evidence