Water → 2-(Benzylthio)-4-(trifluoromethyl)pyridine

Temperature

60 °C

To a solution of phenylmethanethiol (356 μl, 3.03 mmol) and 2-fluoro-4-(trifluoromethyl)pyridine (369 μl, 3.03 mmol) in dimethylformamide (5 mL) was added potassium carbonate (628 mg, 4.54 mmol). The reaction mixture was stirred at 60° C. for 2 hours, then cooled to room temperature, water (10 mL) was added, and the mixture was extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with saturated aqueous sodium hydrogen carbonate solution (20 mL), brine (20 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to give a pale yellow oil. The crude product was purified by chromatography on silica gel (gradient: 0-20% ethyl acetate in isohexane) to afford 2-(benzylthio)-4-(trifluoromethyl)pyridine (510 mg) as a colourless oil. LCMS (Method F, ES-API): RT 3.04 min, m+H=270.1.

1. temperaturecooled to room temperature
2. extractionthe mixture was extracted with ethyl acetate (3×15 mL)
3. washThe combined organic layers were washed with saturated aqueous sodium hydrogen carbonate solution (20 mL), brine (20 mL)
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a pale yellow oil
8. customThe crude product was purified by chromatography on silica gel (gradient: 0-20% ethyl acetate in isohexane)

ORD record

ord-7ff81bb7fb634a4da71dc89d9b744e72

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859774B2