Methyl iodide → 3-Fluoro-4-nitroanisole

HRID 448362Notes

Reaction equation

HRID 448362 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].IC.[C:14](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[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 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-fluoro-4-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 16 hours. The mixture was cooled and evaporated under vacuum, and the partitioned between water (75 mL) and methylene chloride (75 mL) and the aqueous phase was extracted with methylene chloride (2×75 mL). The combined organic phases were washed with water (3×75 mL), dried (MgSO4), and evaporated, providing 5.30 g, in 97% yield: 1H NMR (CDCl3) δ 3.90 (s, 3H), 6.70-6.79 (m, 2H), 8.09 (t, J=9.1 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. temperatureThe mixture was cooled
  4. customevaporated under vacuum
  5. customthe partitioned between water (75 mL) and methylene chloride (75 mL)
  6. extractionthe aqueous phase was extracted with methylene chloride (2×75 mL)
  7. washThe combined organic phases were washed with water (3×75 mL)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customproviding 5.30 g

Sources & evidence

ORD record
ord-83a2820bfee34fe7911a3756d2d40f7a
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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