Water → 1-Benzoyl-6-bromo-2-phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one

HRID 1637255노트

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HRID 1637255 반응식
[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:18](=[O:21])[CH2:19][CH2:20][CH:11]([C:12]=23)[CH:10]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:28]N1C(=O)CCC1=O.O>C(Cl)Cl>[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][C:14]([Br:28])=[C:13]3[C:18](=[O:21])[CH2:19][CH2:20][CH:11]([C:12]=23)[CH:10]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 193483011-Benzoyl-2-phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one

생성물 1

HCID 193483131-Benzoyl-6-bromo-2-phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one수율 83%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A portion (2.0 g) of the compound obtained in Example 1 was dissolved in anhydrous methylene chloride (20 ml) and to the solution was added N-bromosuccinimide (NBS; 1.01 g). The mixture was stirred for 3 days at room temperature. After adding water, the reaction mixture was extracted three times with methylene chloride. The organic layers were combined, washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (methylene chloride/hexane/ethyl acetate=5:5:1) and further crystallized from an ether/hexane mixed solvent to yield 2.02 g (83%) of the titled compound as pale yellow crystals.

후처리

  1. extractionthe reaction mixture was extracted three times with methylene chloride
  2. washwashed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (methylene chloride/hexane/ethyl acetate=5:5:1)
  6. customfurther crystallized from an ether/hexane mixed solvent

출처 및 근거

ORD 기록
ord-d221b8bbd9bb4688ada99bd6cba7f194
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06040331

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