Methyl iodide → 5-Fluoro-2-nitroanisole

HRID 275955Notes

Reaction equation

HRID 275955 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].IC.[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1O)([O-:11])=[O:10]>C(O)C>[F:18][C:15]1[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[C:13]([O:4][CH3:1])[CH:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 27792505-Fluoro-2-nitroanisoleYield 10.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium carbonate(14.5 g, 105.1 mol) and iodomethane(7.1 ml, 114.6 mmol) were added to a solution of 2-nitro-5-fluorophenol(15 g, 95.5 mmol) in ethanol (100 ml), which was then refluxed for 12 hours. The resulting solid was filtered, washed with ethanol, and concentrated. The resulting oily residue was diluted with ethyl acetate and washed with water. The separated organic layer was concentrated and the residual oil was purified by column chromatography(ethylacetate/hexane=1/3) to give 1.65 g of the titled compound. (Yield 9.7%).

Workup

  1. temperaturewas then refluxed for 12 hours
  2. filtrationThe resulting solid was filtered
  3. washwashed with ethanol
  4. concentrationconcentrated
  5. additionThe resulting oily residue was diluted with ethyl acetate
  6. washwashed with water
  7. concentrationThe separated organic layer was concentrated
  8. customthe residual oil was purified by column chromatography(ethylacetate/hexane=1/3)

Sources & evidence

ORD record
ord-d15d2fd2af924096b53f8d91753cf9c4
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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