m-Chloroperbenzoic acid → HCID 86644486, compound

HRID 2404552Notes

Reaction equation

HRID 2404552 reaction equation
[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[C:12]([S:14][CH2:15][C:16]([F:19])([F:18])[F:17])[C:11]([CH3:20])=[CH:10][C:9]=2[F:21])[N:6]=[C:5]([O:22][C:23]([F:32])([F:31])[CH:24]([F:30])[O:25][C:26]([F:29])([F:28])[F:27])[CH:4]=1)#[N:2].ClC1C=CC=C(C(OO)=[O:41])C=1>C(Cl)(Cl)Cl>[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[C:12]([S:14]([CH2:15][C:16]([F:19])([F:18])[F:17])=[O:41])[C:11]([CH3:20])=[CH:10][C:9]=2[F:21])[N:6]=[C:5]([O:22][C:23]([F:32])([F:31])[CH:24]([F:30])[O:25][C:26]([F:27])([F:28])[F:29])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86644485HCID 86644485, compound

Product 1

HCID 86644486HCID 86644486, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.19 g of 5-cyano-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 88 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=1:1) to obtain 0.16 g of 5-cyano-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 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=1:1)

Sources & evidence

ORD record
ord-e7c7284d9fda468497ee3865b8ae9803
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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