Ethyl Acetate → 3-Fluoromethoxy-2-(o-tolyl)-acrylic acid methyl ester

Participants

Reaction Steps

A solution of 14.9 g of bromofluoromethane in 20 ml of dimethylformamide is added dropwise at 10° C. to a solution of 20 g of the sodium salt of 3-hydroxy-2-(o-tolyl)-acrylic acid methyl ester in 125 ml of dimethylformamide and the reaction mixture is then stirred at room temperature for 2.5 hours. The reaction mixture is then poured onto 400 ml of ice-water and exhaustive extraction is carried out with ethyl acetate. Washing with saturated sodium chloride solution is followed by drying over sodium sulfate, filtering and concentration by evaporation. Chromatography on silica gel with hexane/ethyl acetate (6:1) yields pure 3-fluoromethoxy-2-(o-tolyl)-acrylic acid methyl ester in the form of a colourless oil.

Provenance & Evidence