Water → 1-(3-methyl-4-nitro-benzyl)-3-pentafluoroethyl-4-trifluoromethyl-1H-pyrazole

HRID 2243252Notes

Reaction equation

HRID 2243252 reaction equation
I[C:2]1[C:3]([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])=[N:4][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([CH3:17])[CH:9]=2)[CH:6]=1.[F:25][C:26]([Si](C)(C)C)([F:28])[F:27].[F-].[K+].O>CN(C=O)C.[Cu]I>[CH3:17][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[N+:14]([O-:16])=[O:15])[CH2:7][N:5]1[CH:6]=[C:2]([C:26]([F:28])([F:27])[F:25])[C:3]([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])=[N:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 866171374-iodo-1-(3-methyl-4-nitrobenzyl)-3-pentafluoroethyl-1H-pyrazole

Product 1

HCID 866171381-(3-methyl-4-nitro-benzyl)-3-pentafluoroethyl-4-trifluoromethyl-1H-pyrazoleYield 19.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

4-Iodo-1-(3-methyl-4-nitrobenzyl)-3-pentafluoroethyl-1H-pyrazole (1.84 g), (trifluoromethyl)trimethylsilane (1.14 g), copper(I) iodide (1.52 g), potassium fluoride (0.28 g) were stirred in DMF (8 ml) at 100° C. for 8 hours. After cooling, the mixture was poured into water and extracted with ethyl acetate. The combined organic phase was washed with saturated aqueous solution of sodium chloride. After drying the organic layer with sodium sulfate, the solvent was distilled off under the reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 1-(3-methyl-4-nitro-benzyl)-3-pentafluoroethyl-4-trifluoromethyl-1H-pyrazole (0.32 g).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phase was washed with saturated aqueous solution of sodium chloride
  4. dry with materialAfter drying the organic layer with sodium sulfate
  5. distillationthe solvent was distilled off under the reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7e858c576ffa446eb6904954aacdc7eb
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

Loading…