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

HRID 636067
Notes
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Reaction equation

HRID 636067 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 184665183-Fluoro-2-phenylthio-5-trifluoromethylpyridine

Product 1

HCID 184665193-Fluoro-2-phenylsulfinyl-5-trifluoromethylpyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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

  1. stirringThe reaction mixture was stirred at 22° C. for 10 h
  2. extractionextracted with methylene chloride
  3. washThe organic phase was washed with saturated sodium bicarbonate solution and water
  4. customAfter drying
  5. filtrationfiltration
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes