Hydrochloric Acid → 2-(4-Bromo-3-chloro-3,4,4-trifluorobutyl)-2-(2,2,3,4,4,4-hexafluorobutyl)malononitrile

HRID 1443550

Reaction equation

HRID 1443550 reaction equation
[F:1][C:2]([F:15])([CH:9]([F:14])[C:10]([F:13])([F:12])[F:11])[CH2:3][CH:4]([C:7]#[N:8])[C:5]#[N:6].[Cl:16][C:17]([F:25])([CH2:22][CH2:23]Br)[C:18]([Br:21])([F:20])[F:19].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[Br:21][C:18]([F:20])([F:19])[C:17]([Cl:16])([F:25])[CH2:22][CH2:23][C:4]([CH2:3][C:2]([F:15])([F:1])[CH:9]([F:14])[C:10]([F:12])([F:13])[F:11])([C:7]#[N:8])[C:5]#[N:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1362211,4-Dibromo-2-chloro-1,1,2-trifluorobutaneHCID 866125382-(2,2,3,4,4,4-Hexafluorobutyl)malononitrile

Product 1

HCID 866125372-(4-Bromo-3-chloro-3,4,4-trifluorobutyl)-2-(2,2,3,4,4,4-hexafluorobutyl)malononitrileYield 6.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.2 g of 2-(2,2,3,4,4,4-hexafluorobutyl)malononitrile and 1.5 g of 2-chloro-1,4-dibromo-1,1,2-trifluorobutane were dissolved in 10 ml of dimethyl sulfoxide, 0.7 g of potassium carbonate was added, and the mixture was stirred at room temperature for 5 hours. 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 to obtain 0.14 g of 2-(4-bromo-3-chloro-3,4,4-trifluorobutyl)-2-(2,2,3,4,4,4-hexafluorobutyl)malononitrile (hereinafter, referred to as the present compound (46)).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed successively with water and aqueous saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0975f7da5c10463f96adf96a25de6911
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Linked notes

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