Reaction #586137

ord-a1db2cdff5bd4d6f87977ad6496ee5ab

Reaction equation

O=C(OO)c1cccc(Cl)c1
m-chloroperbenzoic acid
FC(F)c1ccc(-c2c[nH]nc2C(F)(F)F)cc1SCC(F)(F)F
[2-difluoromethyl-5-(3-trifluoromethylpyrazolyl)phenyl] 2,2,2-trifluoroethyl sulfide
O=S([O-])[O-].[Na+].[Na+]
sodium sulfite
O=S(CC(F)(F)F)c1cc(-c2c[nH]nc2C(F)(F)F)ccc1C(F)F
[2-difluoromethyl-5-(3-trifluoromethylpyrazolyl)phenyl] 2,2,2-trifluoroethyl sulfoxide
Yield 97.4%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.STIRRINGthe reaction solution was stirred for 1 hour
  2. 2
    workup.STIRRINGstirred at room temperature for 10 minutes
  3. 3
    WashThe chloroform layer was washed with 20 ml of saturated aqueous sodium hydrogen carbonate three times
  4. 4
    Dryingdried over anhydrous magnesium sulfate
  5. 5
    workup.DISTILLATIONthe chloroform was distilled off under reduced pressure

Procedure

To 0.37 g (1.0 mmol) of [2-difluoromethyl-5-(3-trifluoromethylpyrazolyl)phenyl] 2,2,2-trifluoroethyl sulfide (Compound No. V-295 of the present invention) in 5 ml of chloroform, 0.25 g (1.5 mmol) of m-chloroperbenzoic acid was added at 0° C. with stirring, and the reaction solution was stirred for 1 hour. The reaction solution was mixed with 10 ml of 10% aqueous sodium sulfite and stirred at room temperature for 10 minutes, and then 20 ml of chloroform was added. The chloroform layer was washed with 20 ml of saturated aqueous sodium hydrogen carbonate three times and dried over anhydrous magnesium sulfate, and the chloroform was distilled off under reduced pressure to obtain 0.38 g of [2-difluoromethyl-5-(3-trifluoromethylpyrazolyl)phenyl] 2,2,2-trifluoroethyl sulfoxide (yield 97.4%) as a yellow dough (nD2 1.4909).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07767626B2uspto-grants-2010_08