Methyl iodide → 1-Chloro-5-fluoro-2-methoxy-4-nitrobenzene

HRID 2295942Notes

Reaction equation

HRID 2295942 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>[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

5

Reactant 3

HCID 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 962WaterSolvent

Procedure

To a mixture of 2-chloro-4-fluoro-5-nitrophenol (9.6 g) and potassium carbonate (3.8 g) in acetontrile (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-517e1b302d4d4bf8a83f38133172ae2e
Source dataset
uspto-grants-1984_01
Patent number
US04427438

Reaction notes

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