Methyl iodide → 5-Fluoro-2-nitroanisole

HRID 1042708Notes

Reaction equation

HRID 1042708 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+].IC>CN(C=O)C>[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 6228DimethylformamideSolvent

Procedure

5-Fluoro-2-nitrophenol (6 g, 38.2 mmol) was dissolved in anhydrous DMF (20 ml). Potassium carbonate (5.3 g, 38.2 mmol) was added, followed by iodomethane (2.28 ml, 38.2 mmol). The reaction was stirred at room temperature for 16 h, then partitioned between dichloromethane and water. The organic layer was washed three times with 1M sodium hydroxide and once with brine, then dried over sodium sulfate. Removal of the solvent in vacuo afforded the title compound as a yellow oil, which solidified upon standing.

Workup

  1. custompartitioned between dichloromethane and water
  2. washThe organic layer was washed three times with 1M sodium hydroxide
  3. dry with materialonce with brine, then dried over sodium sulfate
  4. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-409c5ff856214ac89c0c633d9cf76e71
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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