Methyl iodide → 2-Methoxy-4-phenoxybromobenzene

HRID 1289181Notes

Reaction equation

HRID 1289181 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[OH:15].[C:16]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[CH3:16][O:15][C:3]1[CH:4]=[C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 189257712-Bromo-5-phenoxyphenol

Product 1

HCID 189257722-Methoxy-4-phenoxybromobenzeneYield 92.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-bromo-5-phenoxyphenol (0.38 g, 1.4 mmol) in 6 ml acetone was added K2CO3 (0.58 g, 4.2 mmol) and iodomethane (0.26 ml, 4.2 mmol). The-reaction mixture was heated to reflux for 8 h, cooled to ambient temperature and filtered. The solvent was removed under reduced pressure and the residue was taken up in EtOAc. The organic phase was washed with 1N NaOH, water and brine. Drying over Na2SO4 afforded 0.36 g (92%) of 2-methoxy-4-phenoxybromobenzene.

Workup

  1. customThe-reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 8 h
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. washThe organic phase was washed with 1N NaOH, water and brine
  7. dry with materialDrying over Na2SO4

Sources & evidence

ORD record
ord-5df851b9137742cdb02a7035877fd118
Source dataset
uspto-grants-1998_05
Patent number
US05747540

Reaction notes

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