Hydrogen Peroxide → Dibenzothiophene sulfoxide

HRID 2262386Notes

Reaction equation

HRID 2262386 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% (w/v) 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-32e7adc7b6ee4cd080f6d24c2da1d693
Source dataset
uspto-grants-2010_12
Patent number
US07851130B2

Reaction notes

Loading…