Potassium Iodide → 1-(2,3-Difluoro-6-nitrophenoxy)propan-2-one

HRID 851079

Reaction equation

HRID 851079 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:12].Cl[CH2:14][C:15](=[O:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH2:14]([O:12][C:3]1[C:2]([F:1])=[C:7]([F:8])[CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10])[C:15]([CH3:16])=[O:17]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 27337452,3-Difluoro-6-nitrophenol

Product 1

HCID 12682411-(2,3-Difluoro-6-nitrophenoxy)propan-2-oneYield 65.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.8 g of 2,3-difluoro-6-nitrophenol, 5.0 g of monochloroacetone, 8.0 g of potassium carbonate and 0.8 g of potassium iodide were added to 100 ml of acetone and the mixture was refluxed for 4 hours. After the removal of insoluble material by filtration, the solvent was evaporated and the residue was distributed between chloroform and water. The chloroform layer was washed with water and was dried, then the solvent was evaporated. The residue was treated with n-hexane to provide 5.0 g of 2-acetonyloxy-3,4-difluoronitrobenzene as light yellow crystals with m.p. 61° C.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customAfter the removal of insoluble material
  3. filtrationby filtration
  4. customthe solvent was evaporated
  5. washThe chloroform layer was washed with water
  6. customwas dried
  7. customthe solvent was evaporated
  8. additionThe residue was treated with n-hexane

Sources & evidence

ORD record
ord-6fb2dfaa0e1c49c2aa2f8266807d0b80
Source dataset
uspto-grants-1983_05
Patent number
US04382892

Linked notes

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