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

HRID 1355681Notes

Reaction equation

HRID 1355681 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-bromobenzylbromide (15.0 g) in methanol-dimethoxyethane (30 ml+10 ml) was added sodium methylate (4.9 g) under cooling with ice and the mixture was stirred for 1 hour at room temperature. The reaction mixture was poured into water. The reaction mixture was extracted with ether. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and the solvent was evaporated to give the title compound (12.1 g) having the following physical data.

Workup

  1. temperatureunder cooling with ice
  2. extractionThe reaction mixture was extracted with ether
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a8b322467f3c44e5a3288a7a153c0cbd
Source dataset
uspto-grants-2003_07
Patent number
US06586468B1

Reaction notes

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