m-Chloroperbenzoic acid → HCID 86644444, compound

HRID 2404518Notes

Reaction equation

HRID 2404518 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]([CH3:20])=[CH:18][C:17]([O:21][CH2:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[N:16]1.ClC1C=CC=C(C(OO)=[O:36])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:14])([F:12])[F:13])=[O:36])=[CH:4][C:3]=1[N:15]1[C:19]([CH3:20])=[CH:18][C:17]([O:21][CH2:22][CH2:23][C:24]([F:25])([F:26])[F:27])=[N:16]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86644443HCID 86644443, compound

Product 1

HCID 86644444HCID 86644444, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.29 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-5-methyl-3-(3,3,3-trifluoropropoxy)pyrazole was dissolved in 10 mL of chloroform, and 0.17 g of m-chloroperbenzoic acid (purity: 75%) was slowly 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 magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (ethyl acetate:hexane=1:2) to obtain 0.30 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl}-5-methyl-3-(3,3,3-trifluoropropoxy)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. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-28ae91cea91d41fda705ec8ace6ceba0
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

Loading…