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

HRID 846505Notes

Reaction equation

HRID 846505 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+].IC>CC(C)=O.C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

6

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 76.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 8.0 g (0.042 mole) of 2-chloro-4-fluoro-5-nitrophenol in 200 mL of acetone was added 6.09 g (0.0435 mole) of potassium carbonate. The mixture was heated at reflux temperature for 15 minutes, and 8.9 g (0.063 mole) of iodomethane was added. The resultant mixture was heated at reflux temperature for 5 hours, then stirred at room temperature for approximately 18 hours. The mixture was filtered and the filtrate evaporated under reduced pressure to leave a residue. The residue was dissolved in diethyl ether, filtered, and the filtrate washed with a saturated sodium chloride solution. The ether solution was dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated to yield 6.6 g of 1-chloro-5-fluoro-2-methoxy-4-nitrobenzene as a solid, 63°-65° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 15 minutes
  3. temperatureat reflux temperature for 5 hours
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated under reduced pressure
  6. customto leave a residue
  7. filtrationfiltered
  8. washthe filtrate washed with a saturated sodium chloride solution
  9. dry with materialThe ether solution was dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe filtrate evaporated

Sources & evidence

ORD record
ord-4256073ea57c4139b0eefbdf6d0451b0
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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