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Pyridine → Bis-(4-butoxyphenyl)phenyl sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate

HRID 277684
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HRID 277684 반응식
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C(C)(C)C)=[CH:16][CH:15]=2)=O)=[CH:8][CH:7]=1)([CH3:4])(C)C.N1[CH:30]=[CH:29][CH:28]=[CH:27]C=1.[F:31][C:32]([F:47])([F:46])[CH:33]([F:45])[C:34]([F:44])([F:43])[S:35]([O:38][Si](C)(C)C)(=[O:37])=[O:36].[Mg].Cl[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>O1CCCC1.ClCCl.O>[F:47][C:32]([F:31])([F:46])[CH:33]([F:45])[C:34]([F:43])([F:44])[S:35]([O-:38])(=[O:36])=[O:37].[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S+:12]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:30][CH2:29][CH2:28][CH3:27])=[CH:18][CH:19]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[CH:10][CH:11]=1)[CH2:4][CH2:32][CH3:33]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 1049PyridineHCID 7964ChlorobenzeneHCID 5462224MagnesiumHCID 15389810Bis(4-tert-butoxyphenyl) sulfoxideHCID 22625546Trimethylsilyl 3,3,3,2,1,1-hexafluoropropane sulfonate

생성물 1

HCID 86757889Bis-(4-butoxyphenyl)phenyl sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
5 °C

실험 절차

To a stirred solution of 60.0 g (0.174 mol) of bis-(4-t-butoxyphenyl) sulfoxide in 26.8 g (0.34 mol) of pyridine and 400 ml of tetrahydrofuran was dropped 75.6 g (0.34 mol) of trimethylsilyl 3,3,3,2,1,1-hexafluoropropane sulfonate while keeping the solution temperature below −5° C. with a salted (sodium chloride) ice bath. After completion of the addition, the reaction temperature was raised to 5° C., followed by stirring for 20 minutes. A Grignard reagent solution was prepared from 8.4 g (0.34 mol) of shaved magnesium, 100 g of tetrahydrofuran and 42.8 g (0.38 mol) of chlorobenzene, and added dropwise to the above solution at 0° C. The mixture was stirred for 2 hours at this temperature. Then water was added to decompose the excess Grignard reagent. The inorganic salts were removed by filtration. The solution was concentrated to about 160 ml and extracted with 1200 ml of dichloromethane, 600 g of a saturated solution of ammonium chloride and 600 ml of water. The organic phase was washed twice with water and dried. The solvent was removed to yield an oily product which was applied to column chromatography on silica gel using dichloromethane as the developing solvent. The corresponding fractions were combined and concentrated to obtain bis-(4-butoxyphenyl)phenyl sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate as a slightly yellowish powder (m.p. 102° C.). The structure was confirmed by 1H-NMR (CDCl3) with δ=1.42 (s, 18H), 5.32-5.54 (d[m], 1H), 7.20-7.23 (d, 4H), and 7.63-7.79 ppm (m, 9H).

후처리

  1. customthe solution temperature below −5° C.
  2. additionAfter completion of the addition
  3. additionadded dropwise to the above solution at 0° C
  4. stirringThe mixture was stirred for 2 hours at this temperature
  5. customThe inorganic salts were removed by filtration
  6. concentrationThe solution was concentrated to about 160 ml
  7. extractionextracted with 1200 ml of dichloromethane, 600 g of a saturated solution of ammonium chloride and 600 ml of water
  8. washThe organic phase was washed twice with water
  9. customdried
  10. customThe solvent was removed
  11. customto yield an oily product which
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a0f502fe3de044ae9ac88b82d5933a2a
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06358665B1

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