Hydrochloric Acid → HCID 86612554, compound

HRID 1443569Notes

Reaction equation

HRID 1443569 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].[Cl:19][C:20]([C:22]([F:25])([F:24])[F:23])=[CH2:21].Cl>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl:19][CH:20]([C:22]([F:25])([F:24])[F:23])[CH2:21][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 3

HCID 313Hydrochloric AcidHCID 27367162-chloro-3,3,3-trifluoroprop-1-eneHCID 25242027(2,2,3,3,4,4,5,5-Octafluoropentyl)propanedinitrile

Product 1

HCID 86612554HCID 86612554, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

1.4 g of 2-(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile was dissolved in 10 ml of a solution (1 mol/L) of tetrabutylammonium fluoride in tetrahydrofuran and thereto 5 ml of 2-chloro-3,3,3-trifluoropropene was added at 0° C. The mixture was then stirred at room temperature for 3 days. 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 0.03 g of 2-(2-chloro-3,3,3-trifluoropropyl)-2-(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile (hereinafter, referred to as the present compound (69)).

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-e769063c420444c5a9f927cc00e5b452
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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