Methyl iodide → N-(4-bromophenyl)-N-methylacetamide

Participants

Reaction Conditions

Reaction Steps

4-bromoacetanilide (1.0 g, 4.67 mmol) in DMF (5 mL) is added dropwise to a suspension of sodium hydride (224 mg, 5.61 mmol, 60% dispersion in mineral oil) in DMF (5 mL) at 0° C. After stirring 1 h at 0° C., iodomethane (349 μl, 5.61 mmol) is added and the reaction mixture warmed to RT and stirred 16 h. The reaction is quenched with water (15 mL) and extracted into EtOAc (3×15 mL); the combined organic phases are then dried over Na2SO4 and reduced in vacuo. Purification by column chromatography (40% EtOAc in heptane) gives the title compound.

Provenance & Evidence