Water → 2-Bromo-5-fluoroanisole

HRID 34014Notes

Reaction equation

HRID 34014 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[C:10](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27246002-Bromo-5-fluorophenol

Product 1

HCID 70180432-Bromo-5-fluoroanisoleYield 90.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g of 2-bromo-5-fluorophenol was dissolved in 105 mL of N,N-dimethylformamide, and added with 10.9 g of potassium carbonate and 4.9 mL of iodomethane under cooling, and stirred at room temperature for 3 hours. The reaction solution was added with water, extracted with diethyl ether, and the resultant organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated, to afford 9.75 g of the title compound as a yellow oil.

Workup

  1. temperatureunder cooling
  2. extractionextracted with diethyl ether
  3. washthe resultant organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-45cd9a0160cb412a851ecc8da71ed727
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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