Methyl iodide → 5-Fluoro-2-nitroanisole

HRID 1269578Notes

Reaction equation

HRID 1269578 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.[C:12](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH3:12])[CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 27792505-Fluoro-2-nitroanisole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Fluoro-2-nitrophenol (10.3 g), potassium carbonate (27.1 g), methyl iodide (11.1 g) and acetone (100 mL) was heated at reflux until the starting materials were consumed. After cooling down to room temperature, the reaction mixture was diluted with ethylacetate, washed with hydrogen chloride (1 N) and brine. After puridication on column (silica gel, ethyl acetate/petrolium ether, 1:9), 10.8 g (96%) of of 5-fluoro-2-nitroanisole was obtained.

Workup

  1. temperatureat reflux until the starting materials
  2. customwere consumed
  3. additionthe reaction mixture was diluted with ethylacetate
  4. washwashed with hydrogen chloride (1 N) and brine

Sources & evidence

ORD record
ord-f655717fa2fa4af5a1c142e581e6d7ce
Source dataset
uspto-grants-2007_04
Patent number
US07199265B2

Reaction notes

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