Ethyl Acetate → 1-(2-Fluorophenyl)-2-methoxy-2-oxoethanaminium chloride

Participants

Reaction Steps

To a suspension of 2-amino-2-(2-fluorophenyl)acetic acid (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (2 g, 11.8 mmol) in MeOH (40 mL) was added thionyl chloride (1.54 g, 13 mmol) dropwise at −10° C. The resulting reaction mixture was stirred for 12 hours at reflux. After completion of the reaction (monitored by TLC, TLC system: 50% EtOAc in hexane), the reaction mixture was cooled to ambient temperature and then concentrated under reduced pressure. The residue was recrystallized with MeOH and diethyl ether to afford 1-(2-fluorophenyl)-2-methoxy-2-oxoethanaminium chloride, 2.5 g (96.30%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.12 (s, 3H), 7.60-7.50 (m, 2H), 7.36-7.29 (m, 2H), 5.45 (s, 1H), 3.73 (s, 3H). m/z (ESI) 184.2 (M+H)+.

Provenance & Evidence