Methyl iodide → 2,6-Difluoroanisole

HRID 1443127Notes

Reaction equation

HRID 1443127 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].[C:10](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 943922,6-Difluorophenol

Product 1

HCID 27368972,6-DifluoroanisoleYield 77.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20 g (153.74 mmol) of 2,6-difluorophenol is dissolved in 200 ml of acetone and mixed under nitrogen with 42.5 g (307.48 mmol) of potassium carbonate. After 19.1 ml of methyl iodide (2 equivalents) is added, it is refluxed for three and one-half hours. After cooling, the reaction mixture is filtered, the filter residue is washed with acetone, and the filtrate is spun in until a dry state is reached. The residue is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane). 17.27 g (77.9%) of the desired product is obtained. It should be noted that the product is slightly volatile. The bath temperature should not exceed 30° C., and the vacuum of the rotary evaporator is to be adapted.

Workup

  1. temperatureit is refluxed for three and one-half hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. washthe filter residue is washed with acetone
  5. customThe residue is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane)

Sources & evidence

ORD record
ord-75f4e510c8fb44ee9545f73a04c13ce8
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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