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

HRID 1612967Notes

Reaction equation

HRID 1612967 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

2-Chloro-4-fluoro-5-nitrophenol (9.6 g) and potassium carbonate (3.8 g) were stirred in acetonitrile (50 ml). Methyl iodide (14 g) was added thereto and refluxed for 3 hours. Water was added to the reaction mixture, followed by extraction with ether. The ether extract was washed with water, dried and concentrated. The residue was recrystallized from ethanol to obtain 8.9 g of 4-chloro-2-fluoro-5-methoxynitrobenzene. M.P., 67.5°-69.8° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. extractionfollowed by extraction with ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-560d7dd3596841dba3f5222acec2c26a
Source dataset
uspto-grants-1993_03
Patent number
US05191105

Reaction notes

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