Hydrochloric Acid → Methyl 2-chloro-4-(methylthio)benzoate

Participants

Reaction Steps

To a solution of methyl 4-bromo-2-chlorobenzoate (1.25 g) in N,N-dimethylformamide (10 ml) was added sodium thiomethoxide (459 mg) under ice-cooling and the mixture was stirred for 2 hr. To the reaction mixture was added 1N hydrochloric acid and the resulting product was extracted 3 times with diethyl ether. The organic layers were combined, washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was applied to silica gel column chromatography (hexane/ethyl acetate=10/1) to give methyl 2-chloro-4-(methylthio)benzoate (835 mg) as a colorless oil.

Provenance & Evidence