Water → HCID 86612566, compound

HRID 1443582Notes

Reaction equation

HRID 1443582 reaction equation
[F:1][C:2]([F:11])([F:10])[CH2:3][CH2:4][CH:5]([C:8]#[N:9])[C:6]#[N:7].Br[CH2:13][CH:14]1[CH2:19][CH2:18][C:17]([F:21])([F:20])[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:20][C:17]1([F:21])[CH2:18][CH2:19][CH:14]([CH2:13][C:5]([CH2:4][CH2:3][C:2]([F:10])([F:11])[F:1])([C:8]#[N:9])[C:6]#[N:7])[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 221857612-(3,3,3-Trifluoropropyl)malononitrileHCID 533503614-(Bromomethyl)-1,1-difluorocyclohexane

Product 1

HCID 86612566HCID 86612566, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.2 g of 2-(3,3,3-trifluoropropyl)malononitrile and 0.76 g of 4-bromomethyl-1,1-difluorocyclohexane were dissolved in 10 ml of N,N-dimethylformamide, 0.99 g of potassium carbonate was added, and the mixture was stirred at room temperature overnight. Thereafter, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with dilute hydrochloric acid 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 0.51 g of 2-(4,4-difluorocyclohexyl)methyl-2-(3,3,3-trifluoropropyl)malononitrile (hereinafter, referred to as the present compound (83)).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with dilute hydrochloric acid and aqueous saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d69aa77bf9b419196e0c4e6731d6d80
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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