Toluene → 1-(4-Chlorobenzenesulfonyl)-5-fluoro-1H-indole

HRID 1793868

반응식

HRID 1793868 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.[OH-].[Na+].C1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 73984-Chlorobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 678615-Fluoroindole

생성물 1

HCID 222201261-(4-Chlorobenzenesulfonyl)-5-fluoro-1H-indole수율 75.9%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매

실험 절차

A mixture of 5-fluoroindole (1.0 g, 7.4 mmole), 4-chlorobenzenesulfonyl chloride (1.6 g, 7.6 mmole), tetra-n-butylammonium hydrogen sulfate (0.05 g), 4N sodium hydroxide (5 mL, 20 mmol), and toluene (6 mL) was stirred at room temperature for 15 h. The mixture was diluted with 10 mL water and extracted with 25 mL ethyl acetate. The organic phase was washed with 10 mL water, 10 mL saturated sodium chloride, and then dried (anhydrous magnesium sulfate). The solution was concentrated under reduced pressure. The residue was recrystallized from ethyl ether/hexane to provide 1-(4-Chlorobenzenesulfonyl)-5-fluoro-1H-indole (1.74 g) m.p. 108–109°.

후처리

  1. extractionextracted with 25 mL ethyl acetate
  2. washThe organic phase was washed with 10 mL water, 10 mL saturated sodium chloride
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. concentrationThe solution was concentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl ether/hexane

출처 및 근거

ORD 기록
ord-616b2c0f6a604a29b66a75f3e1e10247
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022708B2

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