1,2-Dibromoethane → 169674-07-1

HRID 2396827ノート

反応式

HRID 2396827 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 18986290169674-07-1収率 69%

試薬・触媒・溶媒 1

HCID 74236Tetrabutylammonium Bromide触媒

実験手順

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°.

後処理

  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)

出典と根拠

ORDレコード
ord-6100701cd5434f71b1e81d7935d9a09b
出典データセット
uspto-grants-1996_02
特許番号
US05494928

反応ノート

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