1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole → 1-[(4-fluorophenyl)methyl]-4-hydroxy-2-methyl-1H-indole

HRID 3355

Reaction equation

HRID 3355 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([O:18]C)[CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]2[CH3:20])=[CH:4][CH:3]=1.B(Br)(Br)Br.C(Cl)Cl>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([OH:18])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]2[CH3:20])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 108258491-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indoleHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 107535031-[(4-fluorophenyl)methyl]-4-hydroxy-2-methyl-1H-indoleYield 84.2%

Procedure

By the method used in Example 1, Part D, 1.1 g (4.1 mmol) of 1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole was O-demethylated by treating it with 16.4 mL of 1M BBr3 /CH2Cl2 to give 881 mg (84% yield) of crude 1-[(4-fluorophenyl)methyl]-4-hydroxy-2-methyl-1H-indole.

Sources & evidence

ORD record
ord-858e366b919f470e923529fff24917ea
Source dataset
uspto-grants-1998_03
Patent number
US05733923

Linked notes

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