Water → 3-Bromo-1-(P-toluenesulfonyl)indole

HRID 478197ノート

反応式

HRID 478197 の反応式
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[OH-].[Na+].O>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 27632773-Bromo-1h-indole

生成物 1

HCID 112102743-Bromo-1-(P-toluenesulfonyl)indole収率 96%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 241Benzene溶媒

実験手順

To a solution of 3-bromoindole (prepared according to the method described in Synthesis, 1096(1982)) (196 mg, 1.0 mmol) and tosyl chloride (286 mg, 1.5 mmol) in benzene (4.5 mL) was added tetra-n-butylammonium hydrogensulfate (34 mg, 0.1 mmol) and a 5.0% aqueous sodium hydroxide (1.0 mL), and the resulting mixture was refluxed for 1 hour. After the reaction solution was cooled to room temperature, water was added to the reaction solution, and the resulting mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the chloroform layer was concentrated, and the resulting crude product was purified by column chromatography on a silica gel (eluent; hexane:ethyl acetate=6:1) to afford the title compound (335 mg, yield: 96%) as white crystals.

後処理

  1. extractionthe resulting mixture was extracted with chloroform
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. concentrationthe chloroform layer was concentrated
  4. customthe resulting crude product was purified by column chromatography on a silica gel (eluent; hexane:ethyl acetate=6:1)

出典と根拠

ORDレコード
ord-d4eccb9a4fc145d0b357794e9d169fb4
出典データセット
uspto-grants-2003_11
特許番号
US06642228B1

反応ノート

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