Hydrochloric Acid → HCID 178444338, compound

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Reaction Steps

0.08 mol of bromodifluoro(4-cyanophenyl)methane [prepared by the method of A. Haas, M. Spitzer, M. Lieb, Chem. Ber. 121 (1988)] are dissolved in 50 ml of THF; at -78°, 50 ml of a 1.6 molar solution of butyllithium in hexane are added dropwise. The mixture is stirred for 15 minutes, and then a solution of 0.08 mol of 4-(trans-4-pentylcyclohexyl)benzonitrile in 60 ml of THF is added dropwise. The mixture is allowed to warm to 0° and then poured into a mixture of ice and dilute hydrochloric acid. The organic phase is separated off, and the aqueous phase is extracted with ether (50 ml) and dichloromethane (2×25 ml). The organic phases are combined, the solvents are removed by distillation, and the residue is chromatographed on a silica gel column using petroleum ether/ether as the eluent. After the eluate has been evaporated, the residue is recrystallized from ethanol.

Provenance & Evidence