Water → 3-Bromo-1-(P-toluenesulfonyl)indole

HRID 478197노트

반응식

HRID 478197 반응식
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[OH-].[Na+].O>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 27632773-Bromo-1h-indole

생성물 1

HCID 112102743-Bromo-1-(P-toluenesulfonyl)indole수율 96%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 241Benzene용매

실험 절차

To a solution of 3-bromoindole (prepared according to the method described in Synthesis, 1096(1982)) (196 mg, 1.0 mmol) and tosyl chloride (286 mg, 1.5 mmol) in benzene (4.5 mL) was added tetra-n-butylammonium hydrogensulfate (34 mg, 0.1 mmol) and a 5.0% aqueous sodium hydroxide (1.0 mL), and the resulting mixture was refluxed for 1 hour. After the reaction solution was cooled to room temperature, water was added to the reaction solution, and the resulting mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the chloroform layer was concentrated, and the resulting crude product was purified by column chromatography on a silica gel (eluent; hexane:ethyl acetate=6:1) to afford the title compound (335 mg, yield: 96%) as white crystals.

후처리

  1. extractionthe resulting mixture was extracted with chloroform
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. concentrationthe chloroform layer was concentrated
  4. customthe resulting crude product was purified by column chromatography on a silica gel (eluent; hexane:ethyl acetate=6:1)

출처 및 근거

ORD 기록
ord-d4eccb9a4fc145d0b357794e9d169fb4
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642228B1

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