Methyl iodide → 3-Fluoro-4-nitroanisole

HRID 491466Notes

Reaction equation

HRID 491466 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.ClCCl>CC(C)=O>[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

6

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 5656543-Fluoro-4-nitroanisoleYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-fluoro-4-nitro-phenol (25.3 g, 0.16 mol) in acetone (160 ml), potassium carbonate (41.7 g, 0.30 mol) and methyl iodide (20.0 ml, 0.32 mol) are added at ambient temperature. The reaction mixture is stirred at 40 C.° for 3 h. After cooling down to room temperature, dichloromethane is added to the reaction mixture, which is filtrated and evaporated. Dichloromethane is added to the residue and the organic phase is washed with H2O and brine, dried over sodium sulfate and evaporated down to give 2-fluoro-4-methoxy-1-nitro-benzene in 98% yield.

Workup

  1. filtrationis filtrated
  2. customevaporated
  3. additionDichloromethane is added to the residue
  4. washthe organic phase is washed with H2O and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated down

Sources & evidence

ORD record
ord-31d427b164da4674b0c9b430f5361271
Source dataset
uspto-grants-2009_05
Patent number
US07531546B2

Reaction notes

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