Methyl iodide → 3-Fluoro-4-nitroanisole

HRID 2064059Notes

Reaction equation

HRID 2064059 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:9]=[C:10](O)[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15].CI>CC(CC)=O.O>[F:7][C:8]1[CH:9]=[C:10]([O:4][CH3:1])[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 3

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

Product 1

HCID 5656543-Fluoro-4-nitroanisoleYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
40 °C

Procedure

Potassium carbonate (79.0 g, 0.57 mol) was added to a stirred solution of 3-fluoro-4-nitrophenol (45.0 g, 0.29 mol) and methyl iodide (50.0 mL, 0.81 mol) in methylethyl ketone (450 mL) at room temperature. The suspension was stirred at 40° C. for 15 hours and then allowed to cool. The mixture was diluted with water (200 mL) and the organic phase was separated. The aqueous phase was extracted with dichloromethane (2×200 mL). The organic extracts were combined, dried over MgSO4 and evaporated under reduced pressure to give the title compound (48.0 g, 97% yield) as a light yellow solid.

Workup

  1. temperatureto cool
  2. customthe organic phase was separated
  3. extractionThe aqueous phase was extracted with dichloromethane (2×200 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7a84b3f45db740028e181ebba6516030
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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