Ethanol → Dibenzothiophene sulfoxide

HRID 2039108Notes

Reaction equation

HRID 2039108 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH:12]1[C:20]2[C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[S:17][C:16]=2[CH:15]=[CH:14][CH:13]=1.C(O)C>C(Cl)(Cl)Cl>[CH:12]1[C:20]2[C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[S:17](=[O:9])[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 3023DibenzothiopheneHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 13898Dibenzothiophene sulfoxideYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-35 °C

Procedure

A solution of mCPBA (8.27 g, 36.9 mmol) in 71 mL chloroform was added dropwise over 30 minutes to a solution of dibenzothiophene in 89 mL chloroform at −35° C. The reaction mixture was stirred at −35° C. for 1 hour and then warmed up to room. The reaction was quenched with saturated sodium bicarbonate aqueous solution. The organic layer was washed with saturated sodium bicarbonate solution twice and dried over MgSO4, concentrated down to give an off-white solid. The solid was dissolved in refluxing ethanol and slowly cooled to room temperature to give a white crystalline solid Dibenzothiophene 5-oxide (5.65 g, 76%). LCMS-ESI−: calc'd for C12H8OS: 200.26; Found: 200.9 (M+H+).

Workup

  1. temperaturewarmed up to room
  2. customThe reaction was quenched with saturated sodium bicarbonate aqueous solution
  3. washThe organic layer was washed with saturated sodium bicarbonate solution twice
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated down
  6. customto give an off-white solid
  7. dissolutionThe solid was dissolved
  8. temperatureslowly cooled to room temperature

Sources & evidence

ORD record
ord-06a1a99898c049068228ce9160b53586
Source dataset
uspto-grants-2013_11
Patent number
US08575118B2

Reaction notes

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