Chlorine → 1-([1,1'-biphenyl]-2-ylmethyl)-4-hydroxy-2-propyl-1H-indole

Participants

Role	Name	HCID	Charge
Reactant	Chlorine	HCID 24526	—
Reactant	Boron tribromide	HCID 25134	—
Reactant	1-([1,1'-biphenyl]-2-ylmethyl)-4-methoxy-2-propyl-1H-indole	HCID 10641940	—
Product	1-([1,1'-biphenyl]-2-ylmethyl)-4-hydroxy-2-propyl-1H-indole	HCID 10854730	71.1%

Reaction Steps

By the method used in Example 1, Part D, 1.16 g (3.27 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-4-methoxy-2-propyl-1H-indole was O-demethylated by treating it with 13 mL of 1M BBr3 /CH2 Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 794 mg (71% yield) of 1-([1,1'-biphenyl]-2-ylmethyl)-4-hydroxy-2-propyl-1H-indole as an oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05733923
Source dataset	uspto-grants-1998_03
ORD ID	ord-a277cd76b49147da9acb93045c400b7a
Source note	uspto-grants-1998_03