N,O-Dimethylhydroxylamine → 4-Fluoro-N-methoxy-N-methylbenzamide

Participants

Reaction Steps

To a solution of N,O-dimethylhydroxylamine (1.51 mmol; 147 mg) in dry THF (3 mL), under argon, was added at −78° C. nbutyllithium 2.5M (3.02 mmol; 1.21 mL). The mixture was stirred 30 minutes at −78° C., before addition of 4-fluorobenzoyl chloride (1.26 mmol; 150 μL). The reaction was stirred overnight at room temperature, then treated with saturated NH4Cl and extracted with ethyl acetate. Combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo, to give the title compound (66%; 173 mg) as a yellow oil used without further purification.

Provenance & Evidence