Ethanol → Dibenzothiophene sulfoxide

HRID 417563

Reaktionsgleichung

Reaktionsgleichung von HRID 417563
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

Komponenten

5

Edukt 3

HCID 702EthanolHCID 3023DibenzothiopheneHCID 70297m-Chloroperbenzoic acid

Produkt 1

HCID 13898Dibenzothiophene sulfoxideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Reaktionsbedingungen

Temperatur
-35 °C

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1d8ee755930d46418aa6d17a02e1d96f
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088368B2

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