Water → 2-Bromo-5-fluoroanisole

HRID 1983494Notes

Reaction equation

HRID 1983494 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

A total of 10 g of 2-bromo-5-fluoro-phenol was dissolved in 105 ml of N,N-dimethylformamide, 10.9 g of potassium carbonate and 4.9 ml of iodomethane were added under ice-cooling, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, followed by extracting with diethyl ether. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated, to give 9.75 g of the title compound as a yellow oil.

Workup

  1. temperaturecooling
  2. extractionby extracting with diethyl ether
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9fca7bcd9dcf459ebcd0f3dcb9291677
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Reaction notes

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