Methyl iodide → 3-Fluoro-4-nitroanisole

HRID 1608918Notes

Reaction equation

HRID 1608918 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].CI.[C:14](=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH3:14])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 5656543-Fluoro-4-nitroanisoleYield 98%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred solution of 10.6 grams (0.068 mole) of 3-fluoro-4-nitrophenol, 12.0 grams (0.084 mole) of methyl iodide and 18.6 grams (0.135 mole) of potassium carbonate in 150 mL of 2-butanone was heated at 70° C. for about 18 hours. After this time, the reaction mixture was filtered and concentrated under reduced pressure to a residue. The residue was dissolved in diethyl ether, and the solution was washed with water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 11.4 grams of 2-fluoro-4-methoxynitrobenzene. The NMR spectrum was consistent with the proposed structure.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure to a residue
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washthe solution was washed with water
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-657565ef02104afab82ad3ff0afff5f7
Source dataset
uspto-grants-1995_03
Patent number
US05399543

Reaction notes

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