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

HRID 2100653Notes

Reaction equation

HRID 2100653 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+].IC>C(#N)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

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-bromo-3-methyl-phenol (500 mg, 2.67 mmol, 1 eq.) in acetonitrile (5 mL) is added K2CO3 (1.47 g, 10.6 mmol, 4 eq.). The mixture is stirred for 30 minutes at room temperature. Iodomethane (493 mg, 1.3 eq) is then added dropwise via syringe and the mixture is stirred for 12 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The combined organic layers are washed with brine and dried over Na2SO4. After concentration, the residue is purified by silica gel column chromatography (5% EtOAc in hexanes) to give 1-Bromo-4-methoxy-2-methyl-benzene.

Workup

  1. stirringthe mixture is stirred for 12 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe residue is purified by silica gel column chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e90019fe78334a529382725a64dddcdc
Source dataset
uspto-grants-2009_08
Patent number
US07572811B2

Reaction notes

Loading…