Methylamine → 2-(2-bromo-5-fluorophenyl)-N-methylacetamide

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (9.4 mL, 129 mmol) is added to a solution of (2-bromo-5-fluoro-phenyl)-acetic acid (20.0 g, 85.8 mmol) in dry toluene (400 mL). The mixture is heated at reflux for 4 hours and the solvent is removed in vacuo. The remanence is redissolved in dry toluene (400 mL) and cooled to 0° C. 40% methylamine (aq.) (17.7 mL, 515 mmol) is added dropwise at 0-5° C. The mixture is then stirred at ambient temperature for 16 hours, poured onto water (250 mL) and extracted with ethyl acetate (3×200 mL). The combined organic fractions are washed successively with saturated sodium bicarbonate solution (150 mL) and brine (150 mL), dried (MgSO4) and concentrated in vacuo. This gives 16.2 g (77%) of crystalline 2-(2-bromo-5-fluoro-phenyl)-N-methyl-acetamide.

Provenance & Evidence