Hydrochloric Acid → 6,6,6-Trifluoro-5-methyl-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile

HRID 888545Notes

Reaction equation

HRID 888545 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH:13]([CH3:18])[C:14]([F:17])([F:16])[F:15])(=O)=O)=CC=1.[F:20][C:21]([F:31])([F:30])[CH2:22][CH2:23][S:24]([CH2:27][C:28]#[N:29])(=[O:26])=[O:25].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[F:15][C:14]([F:17])([F:16])[CH:13]([CH3:18])[CH2:12][CH2:11][CH:27]([S:24]([CH2:23][CH2:22][C:21]([F:20])([F:30])[F:31])(=[O:25])=[O:26])[C:28]#[N:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 574256712-(3,3,3-Trifluoropropylsulfonyl)acetonitrileHCID 749560864,4,4-Trifluoro-3-methylbutyl p-toluenesulfonate

Product 1

HCID 593784576,6,6-Trifluoro-5-methyl-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrileYield 45.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1.0 g of 4,4,4-trifluoro-3-methylbutyl p-toluenesulfonate and 0.7 g of (3,3,3-trifluoropropylsulfonyl)acetonitrile in 50 ml of dimethyl sulfoxide was added 0.5 g of potassium carbonate at room temperature, and then stirred at the same temperature for 16 hours. To the reaction mixture was added 10% hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.50 g of 6,6,6-trifluoro-5-methyl-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile (hereinafter referred to as the present compound (10)).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fcd3425639bf4c64a6cecf9dd83aef2c
Source dataset
uspto-grants-2012_08
Patent number
US08247612B2

Reaction notes

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