Ethyl isothiocyanate → N-ethyl-2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carbothioamide

Participants

Reaction Steps

An amount (103 mg) of 4-bromo-2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran was dissolved in diethyl ether (0.3 ml); to the solution, 1.68 M n-butyllithium (0.18 ml) was added at 0° C. under a nitrogen atmosphere. After stirring the reaction mixture for 2 minutes, a diethyl ether solution (0.3 ml) of ethyl isothiocyanate (34 mg) was added and the mixture was stirred for 2.5 hours at 0° C. The reaction mixture was diluted with diethyl ether, washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluent; hexane/ethyl acetate=4/1) to give the titled compound (60 mg) as a pale yellow crystal.

Provenance & Evidence