Potassium Carbonate → 1,3-Dibromo-5-[(4-methoxyphenyl)methoxy]benzene

HRID 418092Notes

Reaction equation

HRID 418092 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH2:16][C:15]2[CH:18]=[CH:19][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122803,5-DibromophenolHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 252583101,3-Dibromo-5-[(4-methoxyphenyl)methoxy]benzeneYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3,5-Dibromophenol (10.0 g), 4-methoxybenzyl bromide (8.8 g) and potassium carbonate (27.3 g) were combined in acetone (300 mL) and refluxed for 3 h. Then the insoluble material was removed by filtration, the filtrate was concentrated under reduced pressure and the resulting crude oil was purified on a silica gel column using ethyl acetate and hexanes to give light yellow oil which was then crystallized from hexanes to give the title compound (12.1 g, 82% yield). HRMS calcd for C14H12O2Br2 M+ 369.9203, observed 369.9198.

Workup

  1. temperaturerefluxed for 3 h
  2. customThen the insoluble material was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe resulting crude oil was purified on a silica gel column
  5. customto give light yellow oil which
  6. customwas then crystallized from hexanes

Sources & evidence

ORD record
ord-0d7e910f9c5044ffa98199013007c203
Source dataset
uspto-grants-2012_01
Patent number
US08093253B2

Reaction notes

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