Hydrochloric Acid → (2,2,3,3,4,4,5,5-Octafluoropentyl)propanedinitrile

HRID 1443593Notes

Reaction equation

HRID 1443593 reaction equation
[F:1][C:2]([F:21])([C:12]([F:20])([F:19])[C:13]([F:18])([F:17])[CH:14]([F:16])[F:15])[CH2:3]OS(C(F)(F)F)(=O)=O.[C:22](#[N:26])[CH2:23][C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[F:21][C:2]([F:1])([C:12]([F:19])([F:20])[C:13]([F:17])([F:18])[CH:14]([F:15])[F:16])[CH2:3][CH:23]([C:22]#[N:26])[C:24]#[N:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 27758912,2,3,3,4,4,5,5-Octafluoropentyl trifluoromethanesulfonate

Product 1

HCID 25242027(2,2,3,3,4,4,5,5-Octafluoropentyl)propanedinitrileYield 18.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

15 g of (2,2,3,3,4,4,5,5-octafluoropentyl)trifluoromethanesulfonic acid and 2.6 g of malononitrile were dissolved in 20 ml of dimethyl sulfoxide, 5.5 g of potassium carbonate was added, and the mixture was stirred in a water bath for 3 hours. Thereafter, dilute hydrochloric acid was added to the reaction mixture, followed by extraction with methyl tert-butyl ether. The organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate 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-(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile.

Workup

  1. extractionfollowed by extraction with methyl tert-butyl ether
  2. washThe organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f778d2aa96ea414db37098985e0b93c8
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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