o-Toluenesulfonyl chloride → 4-Bromo-1-(2-methyl-benzenesulfonyl)-1H-indole

HRID 1159763

反応式

HRID 1159763 の反応式
[OH-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20](Cl)(=[O:22])=[O:21]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH3:13])(=[O:22])=[O:21]

参加物

7

反応物 3

HCID 8623o-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 6764944-Bromoindole

生成物 1

HCID 220153344-Bromo-1-(2-methyl-benzenesulfonyl)-1H-indole収率 54%

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

Aq. 2.5 M NaOH (5 mL) was added to a stirring mixture of 4-bromo-1H-indole (1000 mg, 5.3 mmol), 2-methylbenzenesulfonyl chloride (1100 mg, 5.6 mmol) and tetrabutylammonium hydrogen sulfate (173 mg, 0.5 mmol) in DCM (10 mL). The reaction mixture was stirred at ambient temperature overnight. The mixture was diluted with DCM and water and the layers were separated. DCM was washed with water 2 times, dried (MgSO2) and concentrated to give 1.6 g of crude material that was purified using flash chromatography (SiO2, eluent EtOAc:hexane 9:1) giving the title product (1 g, 54%). MS (ESI+) for C15H12BrNO2S m/z 350 (M+H)+.

後処理

  1. customthe layers were separated
  2. washDCM was washed with water 2 times
  3. dry with materialdried (MgSO2)
  4. concentrationconcentrated
  5. customto give 1.6 g of crude material that
  6. customwas purified

出典と根拠

ORDレコード
ord-3218029980604fa5ab77b0b0aeb011a5
出典データセット
uspto-grants-2010_10
特許番号
US07812017B2

関連ノート

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