Water → 1-Bromo-3-(methoxymethyl)benzene

HRID 990907Notes

Reaction equation

HRID 990907 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[CH3:10][O-:11].[Na+].O>CO.C(COC)OC>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH2:5][O:11][CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 699793-Bromobenzyl bromideHCID 10942334Sodium Methoxide

Product 1

HCID 132195821-Bromo-3-(methoxymethyl)benzeneYield 100.3%

Reagents, catalysts & solvents 1

HCID 86595564Dimethoxyethane methanolSolvent

Procedure

To a solution of 3-bromobenzyl bromide (15.0 g, 60 mmol) in methanol-dimethoxyethane (DME) (30 ml+10 ml), sodium methylate (4.9 g, 90 mmol) was added under cooling with ice. The mixture was stirred for 1 hour at room temperature. The reaction mixture was poured into water and extracted with ether. The organic layer was washed by an aqueous saturated solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off to obtain the title compound ( 12.1 g) having the following physical data.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ether
  3. washThe organic layer was washed by an aqueous saturated solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-7c1ea09f1e4c4105b70c03a954a73b7d
Source dataset
uspto-grants-2002_10
Patent number
US06462081B1

Reaction notes

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