Ethyl trifluoroacetate → 4,4,4-Trifluoro-2-(4-fluorophenyl)-3-oxobutanenitrile

Participants

Reaction Steps

Dry ethanol (15 ml) was added to sodium metal (1.22 g, 0.0530 mole) and the mixture was heated under reflux to dissolve sodium metal perfectly. A mixture of ethyl trifluoroacetate (7.53 g, 0.0530 mole) and p-fluorophenylacetonitrile (6.76 g, 0.0500 mole) was added dropwise over 30 minutes. The mixture, after being heated under reflux for 10 hours, was extracted with methylene chloride to remove neutral and basic components. To the mixture was then added 36% hydrochloric acid to adjust below pH 2 and the mixture was extracted with diethyl ether again. After being dried, the solvent was distilled off under reduced pressure to give the crude title compound (10.47 g, 84.0%). The product showed a single spot on thin-layer chromatography. The product was recrystallized from benzenecyclohexane to recover the monohydrate of the title compound (8.97 g, 77.0%) as pale yellow prisms. The structure of this compound was confirmed by IR and NMR.

Provenance & Evidence