Methyl iodide → HCID 22996212, compound

HRID 1167295

Reaction equation

HRID 1167295 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH2:10][CH2:11][CH3:12].[C:13](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:13])=[CH:4][C:3]=1[O:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 229961784-Bromo-3-propoxy-phenol

Product 1

HCID 22996212HCID 22996212, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-bromo-3-propoxy-phenol (500 mg, 2.164 mmol) in acetone (10 mL) were added potassium carbonate (299 mg, 2.164 mmol) and methyl iodide (674 μL, 10.82 mmol). The reaction mixture was heated at gentle reflux for 12 h. The solvent was removed and the residue was taken in diethyl ether (50 mL). The white solid was filtered off, and the filtrated was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 5-10% ethyl acetate in hexanes yielded 1-bromo-4-methoxy-2-propoxy-benzene as a clear oil (515 mg, 97%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat gentle reflux for 12 h
  3. customThe solvent was removed
  4. filtrationThe white solid was filtered off
  5. concentrationthe filtrated was concentrated in vacuo
  6. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  7. washeluting with 5-10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6a9d5e8751a747bb99f4fd51da30ab0c
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Linked notes

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