Hydrogen Peroxide → 3-Fluoro-2-phenylsulfinyl-5-trifluoromethylpyridine

HRID 636067Notes

Reaction equation

[F:1][C:2]1[C:3]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.FC(F)(F)C(O)=[O:22].OO>C(O)(=O)C>[F:1][C:2]1[C:3]([S:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:22])=[N:4][CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

Conditions

Temperature: 22 °C

Procedure

20 g (0.0693 mol) of 95% pure 3-fluoro-2-phenylthio-5-trifluoromethylpyridine were introduced into 100 ml of glacial acetic acid and 20 ml of trifluoroacetic acid and over a period of 5 min, with stirring at 22° C., 5.64 g (0.083 mol) of 50% strength hydrogen peroxide were added. The reaction mixture was stirred at 22° C. for 10 h and then poured into 1 l of ice-water and extracted with methylene chloride. The organic phase was washed with saturated sodium bicarbonate solution and water. After drying, filtration through silica gel and concentration under reduced pressure, 19.1 g (95.4% of theory) of the title compound of 24 n D

Workup

stirringThe reaction mixture was stirred at 22° C. for 10 h
extractionextracted with methylene chloride
washThe organic phase was washed with saturated sodium bicarbonate solution and water
customAfter drying
filtrationfiltration
concentrationthrough silica gel and concentration under reduced pressure, 19.1 g (95.4% of theory) of the title compound of 24 n D

Sources & evidence

ORD record: ord-b9b1d0163ddc4a40b4e2f3efd531e50b
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06191280B1

Reaction notes

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