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

HRID 1637255Notes

Reaction equation

HRID 1637255 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d221b8bbd9bb4688ada99bd6cba7f194
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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