(Trifluoromethyl)benzene → 1H-Imidazole, 1-(1,2,2-trifluoroethenyl)-

HRID 889667Notes

Reaction equation

HRID 889667 reaction equation
C1(C(F)(F)F)C=CC=CC=1.[F:11][C:12]([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)(F)[CH:13]([F:15])[F:14]>O>[F:11][C:12]([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)=[C:13]([F:15])[F:14]

Participants

4

Reactant 2

HCID 7368(Trifluoromethyl)benzeneHCID 132688751-(1,1,2,2-Tetrafluoroethyl)-1H-imidazole

Product 1

HCID 674939581H-Imidazole, 1-(1,2,2-trifluoroethenyl)-Yield 7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Then the entire crude reaction product was poured into water (30 ml), and subjected to extraction with ethyl acetate. After separation of an organic layer, drying was carried out with magnesium sulfate and concentration was conducted under reduced pressure. Then thereto was added 1.46 g (10 mmol) of benzotrifluoride, and it was confirmed by a 19F-NMR analysis based on benzotrifluoride that 1-(1,1,2,2-tetrafluoroethyl)imidazole had been produced at yield of 7% and 1-(1,2,2-trifluoroethenyl)imidazole had been produced at yield of 39%.

Workup

  1. customThen the entire crude reaction product
  2. extractionsubjected to extraction with ethyl acetate
  3. customAfter separation of an organic layer
  4. customdrying
  5. concentrationwas carried out with magnesium sulfate and concentration

Sources & evidence

ORD record
ord-a2870faee1ca4a498a0e24831502def2
Source dataset
uspto-grants-2012_08
Patent number
US08252944B2

Reaction notes

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