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0 °C

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 organic layer was extracted with CH2Cl2 one more time. The combined organic layer was dried over anhydrous Na2SO4, filtered, concentrated, purified on silica gel using 5 percent ethyl acetate in hexane to give 0.348 g of the 2-[chloro(difluoro)methyl]-5-[1-(methylthio)ethyl]pyridine (E) in 40 percent yield GC-MS: mass calcd for C9H10ClF2NS [M]+ 237. Found 237.

1. temperatureto warm to room temperature
2. stirringstirred overnight
3. customThe solvent ethanol was then removed under reduced pressure
4. customThe two phases were separated
5. extractionthe organic layer was extracted with CH2Cl2 one more time
6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. custompurified on silica gel using 5 percent ethyl acetate in hexane