Formic Acid → Formamide, N-(4-bromophenyl)-

Participants

Reaction Steps

A stirred solution of formic acid (2.5 mL, 88% in water) is cooled to 0° C., treated with acetic anhydride (0.82 mL, 9.0 mmol) then warmed to RT over 30 minutes. The solution is then cooled to 0° C. and 4-bromoaniline (500 mg, 3.0 mmol) added dropwise over 5 minutes. After stirring a further 16 h at RT, the reaction mixture is diluted with water (20 mL) and extracted into DCM (3×20 mL). The combined DCM phases are washed with 1 M HCl (20 mL) and aqueous NaHCO3 (20 mL), dried over Na2SO4 and reduced in vacuo. Purification by column chromatography (20% EtOAc in heptane) affords the title compound.

Provenance & Evidence