Water → 1-Chloro-5-fluoro-2-methoxy-4-nitrobenzene

HRID 1379997Notes

Reaction equation

HRID 1379997 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].[C:13](=O)([O-])[O-].[K+].[K+].CI.O>C(#N)C>[Cl:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-

Product 1

HCID 27792951-Chloro-5-fluoro-2-methoxy-4-nitrobenzeneYield 157.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-chloro-4-fluoro-5-nitrophenol (9.6 g) and potassium carbonate (3.8 g) in acetonitrile (50 ml), there was added methyl iodide (14 g), and the resultant mixture was heated under reflux for 3 hours. After being allowed to cool to room temperature (ca. 20° C.), water was added thereto, and the resulting mixture was extracted with ether. The ether extract was washed with water, dried and concentrated. The residue was recrystallized from ethanol to give 8.9 g of 4-chloro-2-fluoro-5-methoxynitrobenzene. M.P., 67.5°-69.8° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. additionwas added
  3. extractionthe resulting mixture was extracted with ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-f50d37ed74fe42378c8b58f01cdc0fc9
Source dataset
uspto-grants-1986_04
Patent number
US04579688

Reaction notes

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