Methyl iodide → 5-Fluoro-2-nitroanisole

HRID 1496942Notes

Reaction equation

HRID 1496942 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.CI.[C:14](=O)([O-])[O-].[K+].[K+]>CN(C)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-nitroanisole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-fluoro-2-nitrophenol (300 mg), methyliodide (0.50 mL) and potassium carbonate (500 mg) were dissolved in dimethylformamide (DMF, 3 mL), and reacted at 50° C. overnight. The dimethylformamide of the reaction mixture was concentrated under reduced pressure, added with water and the organic layer was extracted with ethyl acetate. The organic layer was washed with brine, and the water was removed with sodium sulfate, and the solvent was removed under reduced pressure. The thus obtained compound was used in the subsequent reaction without further purification.

Workup

  1. customreacted at 50° C. overnight
  2. concentrationThe dimethylformamide of the reaction mixture was concentrated under reduced pressure
  3. additionadded with water
  4. extractionthe organic layer was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customthe water was removed with sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe thus obtained compound was used in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-f735c6e3aa0d4eedb41e64ca67f2cf2f
Source dataset
uspto-grants-2015_12
Patent number
US09199944B2

Reaction notes

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