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

HRID 78544Notes

Reaction equation

HRID 78544 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:18][CH2:17][C:16]([F:20])([F:19])[CH2:15][CH2:14]2)(=O)=O)=CC=1.[C-:21]#[N:22].[Na+]>CS(C)=O>[F:20][C:16]1([F:19])[CH2:15][CH2:14][CH:13]([CH2:12][C:21]#[N:22])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 23224632(4,4-Difluorocyclohexyl)methyl 4-methylbenzenesulfonate

Product 1

HCID 668593322-(4,4-Difluorocyclohexyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Example 370B (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)+.

Workup

  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

Sources & evidence

ORD record
ord-ea36f378ddad42ff8c3ab082f6b041da
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

Loading…