2-Thiocresol → 1-(Cyclopropylsulfanyl)-2-methylbenzene

Participants

Reaction Conditions

Reaction Steps

Potassium t-butoxide (994 mg) and bromocyclopropane (2.92 g) were added to a solution of 2-methylbenzenethiol (1.05 g) in dimethyl sulfoxide (10 mL), and the mixture was stirred at 100° C. for 9.5 hours. The reaction solution was cooled to room temperature and brine was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 1-(cyclopropylsulfanyl)-2-methylbenzene as an orange oil (1.41 g, quant.).

Provenance & Evidence