Methyl iodide → 2,6-Difluoroanisole

HRID 1869310Notes

Reaction equation

HRID 1869310 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-37e7861d61644238b2a8f1df34d544f5
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

Loading…