Chloroacetonitrile → 1-Cyanomethyl-3-(2,6-difluorophenyl)pyrazole

HRID 230082Notes

Reaction equation

HRID 230082 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:13]=[CH:12][NH:11][N:10]=1.Cl[CH2:15][C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:16]([CH2:15][N:11]1[CH:12]=[CH:13][C:9]([C:3]2[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[N:10]1)#[N:17]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 178505719HCID 178505719, compound

Product 1

HCID 221694981-Cyanomethyl-3-(2,6-difluorophenyl)pyrazoleYield 47.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. temperatureunder reflux for 5 hours
  2. distillationAfter acetonitrile was distilled off under reduced pressure, ethyl acetate
  3. additionwas added to the residue, which
  4. washwas then washed with a small amount of water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residual product was recrystallized from a mixed solvent of isopropylether and diethyl ether

Sources & evidence

ORD record
ord-3ed4533132e7444dbe7feed887ba50f9
Source dataset
uspto-grants-2009_07
Patent number
US07566683B2

Reaction notes

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