Iodoethane → 7-Bromo-1-ethyl-1H-indole

Reaktionsgleichung

[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.I[CH2:14][CH3:15]>CN(C=O)C>[CH2:14]([N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[Br:3])[CH:9]=[CH:10]1)[CH3:15]

Komponenten

Versuchsvorschrift

To a 60% dispersion of sodium hydride in mineral oil (0.80 g, 21 mmol), suspended in DMF (50 mL), was added 7-bromoindole (2.0 g, 10 mmol) in DMF (15 mL) followed by a solution of iodoethane (1.64 mL, 26.3 mmol). After 20 minutes, the mixture was quenched with saturated NaHCO3, and poured into EtOAc. The organic layer which was separated, washed with saturated NaHCO3, dried (MgSO4) and concentrated to afford 1-ethyl-7-bromoindole as a brown oil which was used without further purification.