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

HRID 1443570Notes

Reaction equation

HRID 1443570 reaction equation
[F:1][C:2]([F:18])([C:9]([F:17])([F:16])[C:10]([F:15])([F:14])[CH:11]([F:13])[F:12])[CH2:3][CH:4]([C:7]#[N:8])[C:5]#[N:6].I[CH2:20][CH2:21][C:22]([F:31])([F:30])[C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25].C(=O)([O-])[O-].[K+].[K+].Cl>COCCOC>[F:30][C:22]([F:31])([C:23]([F:28])([F:29])[C:24]([F:25])([F:26])[F:27])[CH2:21][CH2:20][C:4]([CH2:3][C:2]([F:18])([F:1])[C:9]([F:16])([F:17])[C:10]([F:14])([F:15])[CH:11]([F:13])[F:12])([C:7]#[N:8])[C:5]#[N:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 109697Alkyl iodides, C4-20, gamma-omega-perfluoroHCID 25242027(2,2,3,3,4,4,5,5-Octafluoropentyl)propanedinitrile

Product 1

HCID 866125552-(3,3,4,4,5,5,5-Heptafluoropentyl)-2-(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrileYield 31.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.4 g of 2-(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile and 1.6 g of 1-iodo-3,3,4,4,5,5,5-heptafluoropentane were dissolved in 5 ml of ethylene glycol dimethyl ether, 0.83 g of potassium carbonate was added, and the mixture was stirred at room temperature for 8 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 0.75 g of 2-(3,3,4,4,5,5,5-heptafluoropentyl)-2-(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile (hereinafter, referred to as the present compound (71)).

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-a4ff8a800ac94e348f40032f20dd68a8
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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