Water → 2-(3,3,3-Trifluoropropyl)malononitrile

HRID 2116671Notes

Reaction equation

HRID 2116671 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16].O>CN(C)C=O>[F:16][C:15]([F:18])([F:17])[CH2:14][CH2:13][CH:2]([C:1]#[N:5])[C:3]#[N:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 27251143-Bromo-1,1,1-trifluoropropane

Product 1

HCID 221857612-(3,3,3-Trifluoropropyl)malononitrileYield 69.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

27.6 g of malononitrile was dissolved in 50 ml of N,N-dimethylformamide and 27.6 g of potassium carbonate was added thereto, followed by stirring for 1 hour at room temperature. To the solution was added the mixture of 17.7 g of 1-bromo-3,3,3-trifluoropropane and 20 ml of N,N-dimethylformamide and stirred for 1 hour. Then, the reaction mixture was poured into water and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography to give 11.3 g of 2-(3,3,3-trifluoropropyl)malononitrile.

Workup

  1. additionTo the solution was added
  2. stirringstirred for 1 hour
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained

Sources & evidence

ORD record
ord-34a8772414314278881001490c9ae2ad
Source dataset
uspto-grants-2008_10
Patent number
US07439266B2

Reaction notes

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