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

HRID 1443589Notes

Reaction equation

HRID 1443589 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

Procedure

27.6 g of malononitrile was dissolved in 50 ml of N,N-dimethylformamide, 27.6 g of potassium carbonate was added, and the mixture was stirred at room temperature for 1 hour. Thereafter, a mixture of 17.7 g of 1-bromo-3,3,3-trifluoropropane and 20 ml of N,N-dimethylformamide was added thereto and the mixture was further stirred for 1 hour. Thereafter, the reaction mixture was poured to water and then extracted with diethyl ether. 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 11.3 g of 2-(3,3,3-trifluoropropyl)malononitrile.

Workup

  1. additionwas added
  2. stirringthe mixture was further stirred for 1 hour
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed successively with water and aqueous saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0d3db65d589743999c8ee7fdcc108c2f
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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