Methyl iodide → 1-Bromo-4-methoxy-2-methylbenzene

HRID 1978230Notes

Reaction equation

HRID 1978230 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[C:10](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:10])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 728574-Bromo-m-cresol

Product 1

HCID 1179151-Bromo-4-methoxy-2-methylbenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 0.8 g (4.4 mmol) of 4-bromo-3-methylphenol in 20 mL of acetone was added 1.5 g (10.9 mmol) of potassium carbonate. A yellow slurry was obtained to which was added 0.55 mL (1.25 g, 8.8 mmol) of methyl iodide. The resultant reaction mixture was stirred at ambient temperature for 12.25 hours, filtered and extracted between ethyl ether and water. The layers were separated and the organic phase was washed with sat. Na2SO3 (aq.) solution, dried over MgSO4, filtered and then concentrated in vacuo to a yellow oil. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as a yellow oil.

Workup

  1. customA yellow slurry was obtained to which
  2. customThe resultant reaction mixture
  3. filtrationfiltered
  4. extractionextracted between ethyl ether and water
  5. customThe layers were separated
  6. washthe organic phase was washed with sat. Na2SO3 (aq.) solution
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to a yellow oil
  10. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7647cf71fd434ced9da7c1518b3bfa5c
Source dataset
uspto-grants-2001_05
Patent number
US06235923B1

Reaction notes

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