1,2-Dibromoethane → 169674-07-1

HRID 2396827Notes

Reaction equation

HRID 2396827 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[OH-].[Na+].[Br:13][CH2:14][CH2:15]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:13][CH2:14][CH2:15][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 871105-Chloroindole

Product 1

HCID 18986290169674-07-1Yield 69%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

A solution of 1 g of 5-chloroindole in 30 ml of 1,2-dibromoethane was treated with 30 ml of 28% NaOH and 80 mg of tetrabutyl-ammonium bromide. The mixture was stirred at 50° for 3 hours. The phases were separated and the aqueous phase was extracted with toluene. The combined organic phases were washed with water and dried over sodium sulfate. The solvent was distilled off and the residue was chromatographed over 150 g of silica gel with hexane-ethyl acetate (5:1). There were obtained 1.17 g (69%) of 1-(2-bromoethyl)-5-chloroindole as white crystals with a m.p. of 71°.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with toluene
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was chromatographed over 150 g of silica gel with hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-6100701cd5434f71b1e81d7935d9a09b
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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