Methyl iodide → 2,3-Difluoro-6-nitroanisole

HRID 358884Notes

Reaction equation

HRID 358884 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:12].[C:13](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[F:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27337452,3-Difluoro-6-nitrophenol

Product 1

HCID 27827542,3-Difluoro-6-nitroanisoleYield 106.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20 g (0.114 mole) of 2,3-difluoro-6-nitrophenol (VI) were dissolved in 700 ml of acetone. 18.9 g (0.137 mole) of potassium carbonate and 34.1 g (0.24 mole) of methyl iodide were added to the solution, and the mixture was heated under reflux for 20 hours, whilst stirring. The solvent was then removed from the mixture by evaporation under reduced pressure, and the residue was extracted with ethyl acetate. The ethyl acetate extract was washed with water and dried, and the solvent was removed by evaporation under reduced pressure to give 23.0 g of 3,4-difluoro-2-methoxy-1-nitrobenzene (VII) as a yellow oil [Step (B1)].

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 hours
  3. customThe solvent was then removed from the mixture by evaporation under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. customdried
  8. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-3edc267b0f534fc48314e44229357d05
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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