1-[(2,6-dichlorophenyl)methyl]-4-methoxy-2-methyl-1H-indole → 1-[(2,6-dichlorophenyl)methyl]-4-hydroxy-2-methyl-1H-indole
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][N:10]1[C:18]2[C:13](=[C:14]([O:19]C)[CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]1[CH3:21].B(Br)(Br)Br.C(Cl)Cl>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][N:10]1[C:18]2[C:13](=[C:14]([OH:19])[CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]1[CH3:21]Komponenten
3
Versuchsvorschrift
By the method used in Example 1, Part D, 1.08 g (3.38 mmol) of 1-[(2,6 dichlorophenyl)methyl]-4-methoxy-2-methyl-1H-indole was O-demethylated by treating it with 13.5 mL of 1M BBr3 /CH2Cl2 to give 862 mg (83% yield) of 1-[(2,6-dichlorophenyl)methyl]-4-hydroxy-2-methyl-1H-indole, after chromatography on silica gel (eluted with 20% EtOAc/hexane).
Quellen und Nachweise
- ORD-Eintrag
- ord-996f0a7d980d4f7db95b5a7e4dbfa2a5