m-Chloroperbenzoic acid → HCID 86644487, compound

HRID 2404553Notes

Reaction equation

HRID 2404553 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N:15]1[C:19]([CH2:20][F:21])=[CH:18][C:17]([O:22][C:23]([F:32])([F:31])[CH:24]([F:30])[O:25][C:26]([F:29])([F:28])[F:27])=[N:16]1.ClC1C=CC=C(C(OO)=[O:41])C=1>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9]([CH2:10][C:11]([F:12])([F:13])[F:14])=[O:41])=[CH:4][C:3]=1[N:15]1[C:19]([CH2:20][F:21])=[CH:18][C:17]([O:22][C:23]([F:32])([F:31])[CH:24]([F:30])[O:25][C:26]([F:28])([F:29])[F:27])=[N:16]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86644488HCID 86644488, compound

Product 1

HCID 86644487HCID 86644487, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.17 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-5-fluoromethyl-3-{1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy}pyrazole was dissolved in 10 mL of chloroform, and 78 mg of m-chloroperbenzoic acid (purity: 75%) was added under cooling with ice. After stirring for one hour 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 magnesium sulfate. Then, 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 0.12 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl}-5-fluoromethyl-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 magnesium sulfate
  6. distillationThen, the 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-b4c05fc02bb643088f5a0c1193bc61a7
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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