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

HRID 3348Notes

Reaction equation

HRID 3348 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16]3[C:11](=[C:12]([O:17]C)[CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[CH3:19])=[CH:3][CH:2]=1.B(Br)(Br)Br.ClCl>>[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16]3[C:11](=[C:12]([OH:17])[CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[CH3:19])=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 24526ChlorineHCID 25134Boron tribromideHCID 10806128HCID 10806128, compound

Product 1

HCID 104954091-([1,1'-biphenyl]-4-ylmethyl)-4-hydroxy-2-methyl-1H-indoleYield 77.4%

Procedure

By the method used in Example 1, Part D, 1.3 g (4.0 mmol) of 1-([1,1'-biphenyl]-4-ylmethyl)-4-methoxy-2-methyl-1H-indole was O-demethylated by treating it with 16 mL of 1M BBr3 /CH2 Cl2 to give 970 mg (77% yield) of crude 1-([1,1'-biphenyl]-4-ylmethyl)-4-hydroxy-2-methyl-1H-indole.

Sources & evidence

ORD record
ord-a59e6c8dd5fb48dda0e37c75c7c2b042
Source dataset
uspto-grants-1998_03
Patent number
US05733923

Reaction notes

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