Methoxyacetyl chloride → Ethyl 4-fluoro-3-methoxyacetamidobenzoate

Participants

Reaction Steps

A solution of 2.8 g (15.3 mmol) of ethyl 3-amino-4-fluorobenzoate (cf L. S. Fosdick and A. F. Dodds in J. Amer. Chem. Soc. 65, 2305 (1943)) and 1.56 mL (1.85 g=17.0 mmol) of methoxyacetylchloride in 50 mL chlorobenzene was stirred for 1 hour at 50° C. and then refluxed for 15 minutes. Then the solvent was distilled off in vacuo and the crude product obtained was purified by flash chromatography (silica gel; dichloromethane/ethanol=100:1). The desired compound, initially oily, solidified within a few days. Yield: 3.8 g (98% of theory); Rf value: 0.38 (silica gel; dichloromethane/ethanol=19:1).

Provenance & Evidence