Ethanol → Dibenzothiophene sulfoxide

HRID 1185780

반응식

HRID 1185780 반응식
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

참가 물질

5

반응물 3

HCID 702EthanolHCID 3023DibenzothiopheneHCID 70297m-Chloroperbenzoic acid

생성물 1

HCID 13898Dibenzothiophene sulfoxide수율 76%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

반응 조건

온도
-35 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-6eac2d116d5546e7a1e499320260fb1a
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669234B2

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