p-Toluenesulfonic acid → Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate

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Reaction Steps

Diethyl 2,3,4,5-tetrafluorobenzoylmalonate (2.9 g) and p-toluenesulfonic acid (15 mg) are added to water (5 ml), and the mixture is refluxed for 3 hours. After cooling, the reaction mixture is extracted with dichloromethane. The dichloromethane layer is washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue is purified by silica gel column chromatography (solvent, chloroform: n-hexane=1:1) to give ethyl α-(2,3,4,5-tetrafluorobenzoyl)acetate (0.8 g), m.p. 44.5°-45.5° C.

Provenance & Evidence