Methyl iodide → 2-Bromo-5-methoxy-1,3-dimethylbenzene

HRID 1667302Notes

Reaction equation

HRID 1667302 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CI.[Br:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13](O)=[CH:12][C:11]=1[CH3:18]>CC(C)=O>[Br:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([O:4][CH3:1])=[CH:12][C:11]=1[CH3:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 2359922-Bromo-5-methoxy-1,3-dimethylbenzeneYield 85.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

After 10.4 g of potassium carbonate and 6.80 ml of methyl iodide were added to a solution of 10.0 g of 4-bromo-3,5-dimethylphenol in 100 ml of acetone, the mixture was heated under reflux for 15 hours. The reaction mixture was concentrated under reduced pressure and saturated aqueous ammonium chloride was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 9.18 g of 4-bromo-3,5-dimethylanisole as colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure and saturated aqueous ammonium chloride
  4. additionwas added to the residue
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated
  10. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-3cda5ca34ab4484fb01948da5fa665c5
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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