Methyl iodide → 5-Fluoro-2-nitroanisole

HRID 1593070Notes

Reaction equation

HRID 1593070 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.[H-].[Na+].CI.[C:16](=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH3:16])[CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 99375-Fluoro-2-nitrophenolHCID 10796Cesium carbonateHCID 24758Sodium hydride

Product 1

HCID 27792505-Fluoro-2-nitroanisole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-fluoro-2-nitro-phenol (369 mg, 2.35 mmol) in 5 mL THF, sodium hydride (96 mg, 2.46 mmol) was added at room temperature, followed by methyl iodide (0.88 ml, 14 mmol). The mixture was stirred at room temperature for 10 hours, and then cesium carbonate (744 mg, 2.35 mmol) was added. The mixture was stirred at room temperature for additional 4 hours, then diluted with ethyl acetate and washed with brine. The organic layers were combined and concentrated in vacuo to give a crude residue, which was purified by column chromatography (silica 5-25% EtOAc/hexane) to give pure 4-fluoro-2-methoxy-1-nitro-benzene.

Workup

  1. stirringThe mixture was stirred at room temperature for additional 4 hours
  2. washwashed with brine
  3. concentrationconcentrated in vacuo
  4. customto give a crude residue, which
  5. customwas purified by column chromatography (silica 5-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-24a5e9f2f62d4277831c88d80521f9a4
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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