Chlorine → 2-ethyl-4-hydroxy-1-(2-phenyl-phenylmethyl)-1H-indole

HRID 3367Notes

Reaction equation

HRID 3367 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([O:17]C)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:19][CH3:20].ClCl>B(Br)(Br)Br>[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([OH:17])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 107122801-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-4-methoxy-1H-indole

Product 1

HCID 106162052-ethyl-4-hydroxy-1-(2-phenyl-phenylmethyl)-1H-indoleYield 69.3%

Reagents, catalysts & solvents 1

HCID 25134Boron tribromideSolvent

Procedure

By the method used in Example 1, Part D, 911 mg (2.6 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-4-methoxy-1H-indole was O-demethylated by treating it with 10 mL of 1M BBr3 /CH2 Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 590 mg (69% yield) of 1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-4-hydroxy-1H-indole as an oil.

Workup

  1. customThe crude product was chromatographed on silica gel
  2. washeluted with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-1b52bb60c1944a8bb041ea0a07e47ab6
Source dataset
uspto-grants-1998_03
Patent number
US05733923

Reaction notes

Loading…