Tert-Butylbenzene → Tris(4-tert-butylphenyl)sulfonium perfluorobutanesulfonate

HRID 277690

반응식

HRID 277690 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[F:36][C:37]([F:52])([F:51])[C:38]([F:50])([F:49])[C:39]([F:48])([F:47])[C:40]([F:46])([F:45])[S:41]([OH:44])(=[O:43])=[O:42].[C:53]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([CH3:56])([CH3:55])[CH3:54]>>[F:52][C:37]([F:36])([F:51])[C:38]([F:49])([F:50])[C:39]([F:47])([F:48])[C:40]([F:45])([F:46])[S:41]([O-:44])(=[O:43])=[O:42].[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S+:11]([C:60]2[CH:61]=[CH:62][C:57]([C:53]([CH3:56])([CH3:55])[CH3:54])=[CH:58][CH:59]=2)[C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 4

HCID 7366Tert-ButylbenzeneHCID 9845Trifluoroacetic anhydrideHCID 67815Perfluorobutanesulfonic acidHCID 184321184,4'-Sulfinylbis(tert-butylbenzene)

생성물 1

HCID 16216937Tris(4-tert-butylphenyl)sulfonium perfluorobutanesulfonate수율 60.2%

반응 조건

온도
4 °C

실험 절차

48.18 g (0.15 mol) of bis-(4-t-butylphenyl) sulfoxide (prepared from diphenyl sulfide and t-butyl bromide via FeCl3 catalyzed alkylation and subsequent oxidation with 2-chlorobenzoic acid) was dissolved in 400 ml of 4-t-butylbenzene in a 1-liter three-neck round-bottom flask equipped with a stirrer, a thermometer, a dropping funnel, a condenser and a nitrogen inlet. The mixture was cooled to 4° C. with vigorous stirring. A solution of 63.0 g (0.30 mol) of trifluoroacetic anhydride and 45.0 g (0.15 mol) of nonafluorobutane sulfonic acid was added dropwise thereto, while the temperature was maintained under ice cooling. After completion of the addition, the mixture was stirred for 1 hour. The temperature was returned to room temperature, followed by stirring for additional 15 hours. After standing overnight, two separate phases were formed. The upper phase was removed and discarded. The oily bottom phase of approximately 150 ml volume was diluted with 800 ml of diethyl ether, and washed twice with water and a sodium bicarbonate solution. The organic phase was dried over MgSO4. After removal of the solvent, a semicrystalline solid was obtained. The semicrystalline solid was recrystallized from diethyl ether. Thus, 66.1 g (60.2%) of white crystals of tris-(4-t-butylphenyl) sulfonium nonafluorobutane sulfonate (m.p. 198-200° C.) was obtained.

후처리

  1. customequipped with a stirrer
  2. temperaturewhile the temperature was maintained under ice cooling
  3. additionAfter completion of the addition
  4. customwas returned to room temperature
  5. stirringby stirring for additional 15 hours
  6. waitAfter standing overnight
  7. customtwo separate phases
  8. customwere formed
  9. customThe upper phase was removed
  10. additionThe oily bottom phase of approximately 150 ml volume was diluted with 800 ml of diethyl ether
  11. washwashed twice with water
  12. dry with materialThe organic phase was dried over MgSO4
  13. customAfter removal of the solvent
  14. customa semicrystalline solid was obtained
  15. customThe semicrystalline solid was recrystallized from diethyl ether

출처 및 근거

ORD 기록
ord-3ecd08a53ab345d083ec7a5fe17ed973
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358665B1

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