Potassium Iodide → 1-(3-Chloro-2-fluoro-6-nitrophenoxy)-2-propanone

HRID 851083Notes

Reaction equation

HRID 851083 reaction equation
[Cl:1][C:2]1[C:3]([F:12])=[C:4]([OH:11])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.Cl[CH2:14][C:15](=[O:17])[CH3:16].[I-].[K+]>CC(C)=O>[CH2:14]([O:11][C:4]1[C:3]([F:12])=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])[C:15]([CH3:16])=[O:17]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 131885853-Chloro-2-fluoro-6-nitrophenol

Product 1

HCID 131885861-(3-Chloro-2-fluoro-6-nitrophenoxy)-2-propanoneYield 54.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3 g (15.7 mmols) of 3-chloro-2-fluoro-6-nitrophenol, 3 ml of chloroacetone and 300 mg of potassium iodide in 50 ml of acetone was refluxed for 6 hours while vigorously stirring. After cooling, any insoluble substance was removed by filtration, and the filtrate was concentrated and purified by silica gel (20 g) column chromatography using chloroform as an eluant to provide 2.5 g (54.5% yield) of 2-acetonyloxy-4-chloro-3-fluoronitrobenzene as an oil.

Workup

  1. temperaturewas refluxed for 6 hours
  2. temperatureAfter cooling
  3. customany insoluble substance was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. custompurified by silica gel (20 g) column chromatography

Sources & evidence

ORD record
ord-e7ae9a4e404c437991836646a990e61b
Source dataset
uspto-grants-1983_05
Patent number
US04382892

Reaction notes

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