Ammonium Chloride → O-methyl 2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carbothioate

Participants

Reaction Steps

An amount (65 mg) of 4-bromo-2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran was dissolved in t-butyl methyl ether (2 ml); to the solution, 1.69 M n-butyllithium (0.11 ml) was added at −70° C. under a nitrogen atmosphere and the mixture was stirred for 10 minutes. Then, dimethoxycarbon sulfide (39 mg) was slowly added dropwise to the reaction mixture, which was stirred for 30 minutes at −70° C. To the reaction mixture, a saturated aqueous solution of ammonium chloride was added, followed by extraction with hexane/ethyl acetate (3/1). The resulting organic layers were washed with 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=2/1) to give the titled compound (36 mg) as a colorless oil.

Provenance & Evidence