Methyl iodide → 5-Fluoro-2-nitroanisole

HRID 448357Notes

Reaction equation

HRID 448357 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.IC.[C:14](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH3:14])[CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 27792505-Fluoro-2-nitroanisoleYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-fluoro-2-nitrophenol (5.0 g, 31.8 mmol), iodomethane (13.5 g, 95.4 mmol), and potassium carbonate (16.7 g, 159 mmol) in acetone (80 mL) was heated to reflux for 4 hours. The mixture was cooled and evaporated under vacuum, and the residue was dissolved in ethyl acetate (200 mL) and washed with water (3×250 mL), dried (MgSO4), and evaporated, providing 5.25 g, in 97% yield: 1H NMR (CDCl3) δ 3.97 (s, 3H), 6.69-6.82 (m, 2H), 7.97 (dd, J=8.9 Hz, J=6.0 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. customevaporated under vacuum
  5. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  6. washwashed with water (3×250 mL)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customproviding 5.25 g

Sources & evidence

ORD record
ord-7e4914902d7d42fcb3eaefeb8d16bace
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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