Methyl iodide → 3-Fluoro-4-nitroanisole

HRID 257359Notes

Reaction equation

HRID 257359 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].[C:12](=O)([O-])[O-].[K+].[K+].CI>CC(=O)CC>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[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 88.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture 25.0 g (0.16 mole) of 3-fluoro-4-nitrophenol, 27.6 g (0.20 mole) of potassium carbonate, and 28.4 g (0.20 mole) of methyl iodide in 2-butanone was heated at 70° C. for approximately 17 hours. The reaction mixture was then poured over ice and extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure, leaving 24.35 g of 3-fluoro-4-nitroanisole as a solid residue. The NMR spectrum was consistent with the proposed structure. This product was used in Step B without further purification.

Workup

  1. additionThe reaction mixture was then poured over ice
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cf71f3d808af4b8c9876875778938f39
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Reaction notes

Loading…