Reaction #1909809

ord-2734c8112b27427c90422f28efd949de

Reaction equation

Fc1cccc(F)c1-c1cc[nH]n1
3-(2,6-difluorophenyl)pyrazole
N#CCCl
chloroacetonitrile
O=C([O-])[O-].[K+].[K+]
potassium carbonate
N#CCn1ccc(-c2c(F)cccc2F)n1
1-cyanomethyl-3-(2,6-difluorophenyl)pyrazole
Yield 47.7%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureunder reflux for 5 hours
  2. 2
    workup.DISTILLATIONAfter acetonitrile was distilled off under reduced pressure, ethyl acetate
  3. 3
    workup.ADDITIONwas added to the residue, which
  4. 4
    Washwas then washed with a small amount of water
  5. 5
    DryingThe organic layer was dried over sodium sulfate
  6. 6
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
  7. 7
    OtherThe residual product was recrystallized from a mixed solvent of isopropylether and diethyl ether

Procedure

3.0 g of 3-(2,6-difluorophenyl)pyrazole was dissolved in 20 ml of acetonitrile, and 2.52 g of chloroacetonitrile and 4.61 g of potassium carbonate were added thereto at room temperature, and heated under reflux for 5 hours. After acetonitrile was distilled off under reduced pressure, ethyl acetate was added to the residue, which was then washed with a small amount of water. The organic layer was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was recrystallized from a mixed solvent of isopropylether and diethyl ether to obtain 1.74 g of 1-cyanomethyl-3-(2,6-difluorophenyl)pyrazole.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07037880B2uspto-grants-2006_05