Ethanol → Dibenzothiophene sulfoxide

HRID 71864

反応式

HRID 71864 の反応式
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

参加物

5

反応物 3

HCID 702EthanolHCID 3023DibenzothiopheneHCID 70297m-Chloroperbenzoic acid

生成物 1

HCID 13898Dibenzothiophene sulfoxide収率 76%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

反応条件

温度
-35 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-4c5aa3ae301a45cd92a5eca7ac750ce3
出典データセット
uspto-grants-2014_09
特許番号
US08822430B2

関連ノート

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