2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl 5-bromo-1H-indole-7-carboxylate
Reaktionsgleichung
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:24]=1)[NH:21][CH2:20][CH2:19]2>C(Cl)(Cl)Cl>[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:24]=1)[NH:21][CH:20]=[CH:19]2Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
DDQ (119.3 g. 525.7 mmol) was added in several portions to a solution of ethyl 5-bromo-2,3-dihydro-1H-indole-7-carboxylate (129.1 g, 0.48 mmol) in CHCl3 (1500 mL) and the mixture was stirred for 2 h. The reaction was filtered and the solid was washed with CHCl3 (3×500 mL). The filtrate was washed with 5% NaOH (3×500 mL), H2O (500 mL) and brine (500 mL) then dried over Na2SO4. The solution was evaporated and the residue was recrystallized with EtOH, giving 88 g (69%) of the title compound.