m-Chloroperbenzoic acid → HCID 86644439, compound

HRID 2404515Notes

Reaction equation

HRID 2404515 reaction equation
[Cl:1][C:2]1[C:3]([O:21][C:22]([F:31])([F:30])[CH:23]([F:29])[O:24][C:25]([F:28])([F:27])[F:26])=[N:4][N:5]([C:7]2[CH:12]=[C:11]([S:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:10]([CH3:19])=[CH:9][C:8]=2[F:20])[CH:6]=1.ClC1C=CC=C(C(OO)=[O:40])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([O:21][C:22]([F:31])([F:30])[CH:23]([F:29])[O:24][C:25]([F:26])([F:27])[F:28])=[N:4][N:5]([C:7]2[CH:12]=[C:11]([S:13]([CH2:14][C:15]([F:18])([F:17])[F:16])=[O:40])[C:10]([CH3:19])=[CH:9][C:8]=2[F:20])[CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86644440HCID 86644440, compound

Product 1

HCID 86644439HCID 86644439, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.24 g of 4-chloro-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-{1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy}pyrazole was dissolved in 10 mL of chloroform, and 0.11 g of m-chloroperbenzoic acid (purity: 75%) was added under cooling with ice. After stirring for 30 minutes under cooling with ice, the solution was washed with an aqueous sodium thiosulfate solution and then washed with an aqueous sodium hydrogen carbonate solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:2) to obtain 0.21 g of 4-chloro-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl}-3-{1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy}pyrazole.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. washthe solution was washed with an aqueous sodium thiosulfate solution
  4. washwashed with an aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-6c65d23639384e37b628393483117e8a
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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