Hydrogen Peroxide → Dibenzothiophene sulfoxide

HRID 909986

Reaction equation

HRID 909986 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH:14]O.O>FC(F)(F)C(O)=O>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6](=[O:14])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 3023Dibenzothiophene

Product 1

HCID 13898Dibenzothiophene sulfoxide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

Dibenzothiophene (20.0 g) is suspended in 80.0 ml of trifluoroacetic acid at room temperature. To the suspension is slowly dropped 12.4 ml of 30% aqueous hydrogen peroxide while cooling with ice so as to maintain the reaction temperature around 60° C. After completion of dropping, the reaction solution is stirred at room temperature for 30 minutes. After the reaction, the reaction solution is added to 1,000 ml of water to precipitate crystals. The crystals are recovered by filtration and washed with water. The obtained crystals are recrystallized with acetonitrile to obtain 19.2 g of dibenzothiophene-S-oxide.

Workup

  1. temperaturewhile cooling with ice so as
  2. customAfter the reaction
  3. customto precipitate crystals
  4. filtrationThe crystals are recovered by filtration
  5. washwashed with water
  6. customThe obtained crystals are recrystallized with acetonitrile

Sources & evidence

ORD record
ord-9216a22ca85c497ea02407fad91d4517
Source dataset
uspto-grants-2011_09
Patent number
US08021819B2

Linked notes

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