Hydrochloric Acid → 2,2-Bis(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile

HRID 1443552Notes

Reaction equation

HRID 1443552 reaction equation
FC(F)(F)S(O[CH2:7][C:8]([F:19])([F:18])[C:9]([F:17])([F:16])[C:10]([F:15])([F:14])[CH:11]([F:13])[F:12])(=O)=O.C(=O)([O-])[O-].[K+].[K+].[C:28](#[N:32])[CH2:29][C:30]#[N:31].Cl>CS(C)=O>[F:18][C:8]([F:19])([C:9]([F:16])([F:17])[C:10]([F:14])([F:15])[CH:11]([F:13])[F:12])[CH2:7][C:29]([CH2:7][C:8]([F:18])([F:19])[C:9]([F:16])([F:17])[C:10]([F:14])([F:15])[CH:11]([F:12])[F:13])([C:28]#[N:32])[C:30]#[N:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 11430Potassium Carbonate2×HCID 27758912,2,3,3,4,4,5,5-Octafluoropentyl trifluoromethanesulfonate2×

Product 1

HCID 159795582,2-Bis(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrileYield 1.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

14.6 g of 2,2,3,3,4,4,5,5-octafluoropentyl trifluoromethanesulfonate was dissolved in 30 ml of dimethyl sulfoxide, and 5.5 g of potassium carbonate was added. Further, 2.6 g of malononitrile dissolved in 10 ml of dimethyl sulfoxide was added dropwise, and the mixture was stirred at room temperature for 3 hours. Further, 7.0 g of 2,2,3,3,4,4,5,5-octafluoropentyl trifluoromethanesulfonate and 2.7 g of potassium carbonate were added, and the mixture was stirred for 1 hour. Thereafter, dilute hydrochloric acid was added to the reaction mixture, followed by extraction with ethyl acetate. 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. The resulting fraction was concentrated and washed with chloroform to obtain 0.13 g of 2,2-bis(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile (hereinafter, referred to as the present compound (49)).

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred for 1 hour
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed successively with water and aqueous saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe resulting fraction was concentrated
  8. washwashed with chloroform

Sources & evidence

ORD record
ord-8624909e9f034d38afe44c66a3530fcb
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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