Sodium Cyanide → 2-(4,4-Difluorocyclohexyl)acetonitrile

Temperature

80 °C

To a solution of Example 184B (4.5 g, 15 mmol) in dimethylsulfoxide (100 mL) was added sodium cyanide (Aldrich, 2.2 g, 45 mmol). The reaction mixture was stirred at 80° C. for 14 hours, cooled to room temperature, quenched with saturated aqueous NaHCO3 (50 mL) and extracted with diethyl ether (3×50 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 50% pentane in ether) to afford the title compound. MS (ESI+) m/z 177 (M+NH4)+.

1. temperaturecooled to room temperature
2. customquenched with saturated aqueous NaHCO3 (50 mL)
3. extractionextracted with diethyl ether (3×50 mL)
4. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by column chromatography

ORD record

ord-d89e9e63685f494fb88478ffe024fed5

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875639B2