Water → 1-Benzyl-5-Bromo-1H-Indole

HRID 583601ノート

反応式

HRID 583601 の反応式
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C)C=O>[CH2:13]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([Br:3])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 14797Potassium HydroxideHCID 249055-Bromoindole

生成物 1

HCID 2857561-Benzyl-5-Bromo-1H-Indole収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
30 °C

実験手順

In a suspension of 26.6 g of KOH in 200 ml of dimethylformamide, 20.1 g of solid 5-bromoindole was incorporated while being stirred. The mixture was stirred for 50 minutes at room temperature, and 25.4 g of benzyl chloride was dropwise added to the mixture over a period of 16 minutes at a temperature of not higher than 30° C. The reaction mixture was maintained at 30° C. in an oil bath for 5 hours with stirring. After completion of the reaction, 200 ml of water was added and the thus-formed aqueous phase was extracted with 120 ml of ether three times. The thus-obtained organic phase was washed with water and dried over sodium sulfate overnight. The dried product was concentrated to dryness and then recrystallized from isopropyl ether to give 23.5 g of N-benzyl-5-bromoindole. The yield was 80% by mole.

後処理

  1. stirringThe mixture was stirred for 50 minutes at room temperature
  2. stirringwith stirring
  3. additionwas added
  4. extractionthe thus-formed aqueous phase was extracted with 120 ml of ether three times
  5. washThe thus-obtained organic phase was washed with water
  6. dry with materialdried over sodium sulfate overnight
  7. concentrationThe dried product was concentrated to dryness
  8. customrecrystallized from isopropyl ether

出典と根拠

ORDレコード
ord-7b241651f8db4175b431fd2f7a415335
出典データセット
uspto-grants-1999_07
特許番号
US05929281

反応ノート

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