Benzenesulfonyl chloride → 4-Bromo-6-methoxy-1-(phenylsulfonyl)-1H-indole

HRID 1159781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159781
[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20]

Komponenten

6

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 247280264-bromo-6-methoxy-1H-indole2×

Produkt 1

HCID 687186244-Bromo-6-methoxy-1-(phenylsulfonyl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Bromo-6-methoxy indole (0.07 g, 0.3 mmol) was dissolved in dry dichloromethane (4 mL) and benzenesulphonyl chloride (0.06 g, 0.3 mmol), tetrabutylammonium hydrogen sulphate (0.01 g, 0.01 mmol) and 4N NaOH (0.5 mL) were added and the mixture was stirred at rt for 50 min. The mixture was extracted with water (2×4 mL), dried (Na2SO4) and evaporated. The crude product was combined with an earlier batch of this intermediate (followed this experimental and starting with 4-bromo-6-methoxy indole (0.35 g, 1.5 mmol). MS (ESI+) for C15H12BrNO3S m/z 366 (M+H)+.

Aufarbeitung

  1. extractionThe mixture was extracted with water (2×4 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e6b77c22118a43229d702192b50cc658
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812017B2

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