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

HRID 1159752

Reaktionsgleichung

Reaktionsgleichung von HRID 1159752
[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]

Komponenten

7

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 6764944-Bromoindole

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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)+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-19adf0d4a9a74c9b8e6b5311acd2efe8
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812017B2

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