Hydrochloric Acid → 2-(2,2,3,3,4,4,5,5-Octafluoropentyl)-2-(3,4,4-trifluoro-3-butenyl)malononitrile

HRID 1443574Notes

Reaction equation

HRID 1443574 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].Br[CH2:20][CH2:21][C:22]([F:26])=[C:23]([F:25])[F:24].C(=O)([O-])[O-].[K+].[K+].Cl>COCCOC>[F:1][C:2]([F:18])([C:9]([F:16])([F:17])[C:10]([F:14])([F:15])[CH:11]([F:13])[F:12])[CH2:3][C:4]([CH2:20][CH2:21][C:22]([F:26])=[C:23]([F:25])[F:24])([C:7]#[N:8])[C:5]#[N:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 663334-Bromo-1,1,2-trifluorobut-1-eneHCID 25242027(2,2,3,3,4,4,5,5-Octafluoropentyl)propanedinitrile

Product 1

HCID 866125592-(2,2,3,3,4,4,5,5-Octafluoropentyl)-2-(3,4,4-trifluoro-3-butenyl)malononitrileYield 23.2%

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 1.3 g of 1-bromo-3,4,4-trifluoro-3-butene were dissolved in 10 ml of ethylene glycol dimethyl ether, 0.97 g of potassium carbonate was added, and the mixture was stirred at room temperature for 10 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 0.45 g of 2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,4,4-trifluoro-3-butenyl)malononitrile (hereinafter, referred to as the present compound (75)).

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-ec8eda03ffed4899be38a43a33d7ca66
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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