Boron tribromide → 3-(2-(Dimethylamino)ethoxy)phenol

HRID 2413176Notes

Reaction equation

[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([O:12]C)[CH:9]=[CH:10][CH:11]=1.B(Br)(Br)Br>>[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 100813693-(2-(Dimethylamino)ethoxy)anisole

Product 1

HCID 204305153-(2-(Dimethylamino)ethoxy)phenol

Procedure

3-(2-(Dimethylamino)ethoxy)anisole is reacted with boron tribromide to give 3-(2-(dimethylamino)ethoxy)phenol which is reacted with sodium hydride and N-(3-bromopropyl)phthalimide and the product deprotected with methylamine to give 3-(3-(2-(dimethylamino)ethoxy)phenoxy)propylamine.

Sources & evidence

ORD record: ord-5ad13c7b173d46f8987c30b12cc4be0d
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04496567

Reaction notes

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