Ammonium Acetate → 1-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanone (0.44 g, 1.6 mmol) and ammonium acetate (1.8 g, 23 mmol) in acetonitrile (3.0 mL) and methanol (3.0 mL) was heated at 65° C. for an hour. Sodium cyanoborohydride (0.244 g, 3.88 mmol) was added and the mixture was heated at 65° C. overnight. Purification by preparative LCMS (pH=10) gave the desired compound (23% yield). LCMS calculated for C9H8BrClFO (M−NH2)+: m/z=264.9, 266.9. found: 264.9, 266.9. 1H NMR (300 MHz, CDCl3): δ 8.81 (br s, 2H), 7.80 (s, 1H), 4.80 (m, 1H), 3.97 (s, 3H), 1.69 (m, 3H).

Provenance & Evidence