3-Bromophenol → [2-(3-Bromophenoxy)ethyl]dimethylamine

HRID 1700909Notes

Reaction equation

HRID 1700909 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:10][N:11]([CH2:13][CH2:14]Cl)[CH3:12].CN(CCOC1C=CC(Br)=CC=1)C>>[CH3:10][N:11]([CH2:13][CH2:14][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH3:12]

Participants

4

Reactant 3

HCID 115633-BromophenolHCID 213877(2-(4-Bromophenoxy)ethyl)dimethylamineHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 413371[2-(3-Bromophenoxy)ethyl]dimethylamineYield 74%

Procedure

3-Bromophenol (5.0 g, 28.9 mmol) and 2-(N,N-dimethylamino)ethyl chloride, hydrochloride (6.24 g, 43.3 mmol) were reacted by the general procedures as described in the preparation of N,N-dimethyl-2-(4-bromophenoxy)ethylamine. The residue was chromatographed on silica gel (dichloromethane/methanol 100:0 to 90:10) to give the title compound (5.2 g, 74%) as a pale yellow liquid.

Workup

  1. customThe residue was chromatographed on silica gel (dichloromethane/methanol 100:0 to 90:10)

Sources & evidence

ORD record
ord-6f4393d8e74a414cb0a7d8a4bbb29ce9
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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