4-Toluenesulfonyl chloride → 4-Bromo-1-(toluene-4-sulfonyl)-1H-indole

HRID 1159752

반응식

HRID 1159752 반응식
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

참가 물질

7

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 6764944-Bromoindole

생성물 1

HCID 5628694-Bromo-1-(toluene-4-sulfonyl)-1H-indole수율 94%

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

4-Bromoindole (1.24 g, 6.3 mmol), p-toluenesulfonyl chloride (1.32 g, 6.9 mmol) and tetrabutyl-ammonium hydrogen sulfate (42 mg, 0.1 mmol) was dissolved in DCM (50 mL). NaOH 2.5 M aq (6 mL, 15 mmol) was added and the mixture was stirred vigorously for 1 h. Diluted with water and DCM, collected the DCM phase and washed it twice with water, dried and concentrated to give the product as white crystalline material (2.07 g, 5.9 mmol). Yield 94%. MS (ESI+) for C15H12BrNO2S m/z 352 (M+H)+.

후처리

  1. customcollected the DCM phase
  2. washwashed it twice with water
  3. customdried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-19adf0d4a9a74c9b8e6b5311acd2efe8
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812017B2

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