Water → 2-(2,2,3,4,4,4-Hexafluorobutyl)malononitrile

HRID 1443591Notes

Reaction equation

HRID 1443591 reaction equation
FC(F)(F)S(O[CH2:7][C:8]([F:16])([F:15])[CH:9]([F:14])[C:10]([F:13])([F:12])[F:11])(=O)=O.C(=O)([O-])[O-].[K+].[K+].[C:25](#[N:29])[CH2:26][C:27]#[N:28].O>CS(C)=O>[F:15][C:8]([F:16])([CH:9]([F:14])[C:10]([F:13])([F:12])[F:11])[CH2:7][CH:26]([C:25]#[N:29])[C:27]#[N:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 588790322,2,3,4,4,4-Hexafluorobutyl trifluoromethanesulfonate

Product 1

HCID 866125382-(2,2,3,4,4,4-Hexafluorobutyl)malononitrileYield 34.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

8.0 g of 2,2,3,4,4,4-hexafluorobutyl trifluoromethanesulfonate was dissolved in 15 ml of dimethyl sulfoxide, and 6.9 g of potassium carbonate was added. 5.0 g of malononitrile dissolved in 15 ml of dimethyl sulfoxide was added dropwise thereto, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured to water and then extracted with diethyl ether. The organic layer was washed successively with water and aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.0 g of 2-(2,2,3,4,4,4-hexafluorobutyl)malononitrile.

Workup

  1. additionwas added dropwise
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed successively with water and aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ddbd3d1c4477408fb7b939e626d48f80
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

Loading…