Dimethyl Sulfoxide → Ethanone, 1-[4-fluoro-2-(methylamino)phenyl]-2-(methylsulfinyl)-

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Reaction Steps

A solution of t-butyl 4-fluoro-2-methylaminobenzoate (28.9 g) in dimethylsulphoxide (133 ml) was added to a solution of potassium t-butoxide (72.2 g) in dimethylsulphoxide (300 ml) at ambient temperature under nitrogen. The stirred mixture was heated at 50° for eight hours and then cooled to ambient temperature. Water (1300 ml) was added to the mixture whilst maintaining the temperature below 35°. Extraction with trichloromethane and evaporation of the extract in vacuo gave 1-(4-fluoro-2-methylaminophenyl)-2-methylsulphinylethanone, m.p. 129°-134°.

Provenance & Evidence