Methyl iodide → 2-Bromo-5-fluoroanisole

HRID 1436905Notes

Reaction equation

HRID 1436905 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].CI.[C:12](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH3:12]

Participants

5

Reactant 3

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

Product 1

HCID 70180432-Bromo-5-fluoroanisoleYield 96.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 15 ml of N,N-dimethylformamide were dissolved 3.94 g of 2-bromo-5-fluorophenol and 1.62 ml of methyl iodide, slowly added thereto was 5.08 g of potassium carbonate under ice-cooling. The mixture was stirred at room temperature for 3 hours. After insoluble matters were removed by filtration, distilled water was added to the filtrate, and the mixture was extracted with diethyl ether and washed with saturated brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography-(hexane:ethyl acetate=19:1→9:1), to give 4.10 g of 1-bromo4-fluoro-2-methoxybenzene.

Workup

  1. additionslowly added
  2. temperaturecooling
  3. customAfter insoluble matters were removed by filtration
  4. distillationdistilled water
  5. additionwas added to the filtrate
  6. extractionthe mixture was extracted with diethyl ether
  7. washwashed with saturated brine
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography-(hexane:ethyl acetate=19:1→9:1)

Sources & evidence

ORD record
ord-24167c9b434944bda48fea8b529bc296
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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