Potassium Carbonate → 4-Bromo-1-methoxy-2-(3-methoxypropoxy)benzene

HRID 744855Notes

Reaction equation

HRID 744855 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][CH2:9][CH2:10][CH2:11]Br.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([O:21][CH3:22])=[C:18]([OH:20])[CH:19]=1>C(#N)C>[CH3:22][O:21][C:17]1[CH:16]=[CH:15][C:14]([Br:13])=[CH:19][C:18]=1[O:20][CH2:11][CH2:10][CH2:9][O:8][CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1422285-Bromo-2-methoxyphenolHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 214587114-Bromo-1-methoxy-2-(3-methoxypropoxy)benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

66.0 g of potassium carbonate and 3-methoxy-1-bromopropane are added at room temperature to a solution of 64.6 g of 5-bromo-2-methoxyphenol in 350 ml of acetonitrile. The reaction mixture is stirred under reflux for 14 hours. After removal of the solvent by evaporation, 1200 ml of ice/water are added to the residue and extraction is carried out with ether. The organic extracts are washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated by evaporation. Distillation under a high vacuum yields the title compound: Re (hexane/ethyl acetate=4:1)=0.33; b.p.=126°-129° C./1.4 mbar; HPLC Rt =16.38 minutes; MS (M+)=274, 276.

Workup

  1. temperatureunder reflux for 14 hours
  2. customAfter removal of the solvent
  3. customby evaporation, 1200 ml of ice/water
  4. additionare added to the residue and extraction
  5. washThe organic extracts are washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated by evaporation
  8. distillationDistillation under a high vacuum

Sources & evidence

ORD record
ord-3557d316fe84436e86d77758d71da234
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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