Diethyl Ether → 1-methyl-3-(4-methylphenyl)-1H-indole

Reaktionsgleichung

Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:11])[CH:3]=1.CCO[CH2:15][CH3:16].[NH4+].[Cl-]>>[CH3:11][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([C:5]2[CH:10]=[CH:9][C:15]([CH3:16])=[CH:7][CH:6]=2)=[CH:3]1

Komponenten

Edukt 3

HCID 3283Diethyl Ether

HCID 25517Ammonium Chloride

HCID 133577363-Bromo-1-methyl-1H-indole

Produkt 1

HCID 589315421-methyl-3-(4-methylphenyl)-1H-indole

Versuchsvorschrift

A mixture of 4.31 g (0.02 mol) of 3-bromo-1-methyl-1H-indole and 0.22 g (0.0004 mol) of NiCl2dppp was added to a solution of p-TolylMgBr in ether (prepared from 0.6 g of Mg (0.025 mol) and 4.21 g of TolylBr (0.024 mol) in 40 mL of ether) under stirring. The reaction mixture was stirred overnight. The resulting mixture was treated with 10% aqueous NH4Cl, the organic layer was separated, washed with 10% aqueous NH4Cl and then dried over anhydrous Na2SO4. The solution was evaporated to give an oil that crystallized. The product was washed with methanol and dried. Yield 2.2 g (49%) of colorless crystalline solid.