2-Methoxy-4-Methylphenol → 1-(3-Bromo-propoxy)-2-methoxy-4-methyl-benzene

HRID 734402

Reaction equation

HRID 734402 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[OH:10].[Br:11][CH2:12][CH2:13][CH2:14]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Br:11][CH2:12][CH2:13][CH2:14][O:10][C:4]1[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 71442-Methoxy-4-MethylphenolHCID 80011,3-DibromopropaneHCID 10796Cesium carbonate

Product 1

HCID 431354281-(3-Bromo-propoxy)-2-methoxy-4-methyl-benzeneYield 42.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-methoxy-4-methylphenol (500 mg, 3.62 mmol) in acetonitrile (20 mL) was added 1,3-dibromopropane (3.65 g, 201.89 mmol) followed by cesium carbonate (2.35 g, 7.24 mmol). The resulting solution was heated at 85° C. for 48 h, then cooled to rt. The solution was filtered through a Celite® pad. The Celite® was washed with acetone, and the combined filtrates were concentrated under reduced pressure to give the title compound as a white solid (395 mg, 42%). GC/MS (EI) m/z 258 (M)+, RT 7.94 min.

Workup

  1. temperaturecooled to rt
  2. filtrationThe solution was filtered through a Celite® pad
  3. washThe Celite® was washed with acetone
  4. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-376c3a1649d241508d7d643ee1f16ae9
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Linked notes

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