Sodium methanethiolate → 2-[Chloro(difluoro)methyl]-5-[1-(methylthio)ethyl]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[chloro(difluoro)methyl]-5-(1-chloroethyl)pyridine (D) (0.81 g, 3.6 mmol) in ethanol (10 mL) was added sodium thiomethoxide (0.52 g, 7.4 mmol) under stirring in one portion at 0° C. After 10 min, the mixture was allowed to warm to room temperature and stirred overnight. The solvent ethanol was then removed under reduced pressure and the residue was re-taken into ether/CH2Cl2 and brine. The two phases were separated and the aqueous layer was extracted with CH2Cl2 one more time. The combined organic layer was dried over anhydrous Na2SO4, filtered, concentrated, and purified on silica gel using 5% ethyl acetate in hexane (v/v) to give 0.348 g of the 2-[chloro(difluoro)methyl]-5-[1-(methylthio)ethyl]pyridine (E) in 40% yield GC-MS: mass calcd for C9H10ClF2NS [M]+ 237. Found 237.

Provenance & Evidence