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

HRID 1159763

Reaktionsgleichung

Reaktionsgleichung von HRID 1159763
[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]

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3218029980604fa5ab77b0b0aeb011a5
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812017B2

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