Sodium Acetate → 2-Acetoxy-2',4'-difluoroacetophenone

HRID 1591341Notes

Reaction equation

HRID 1591341 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=[O:4].[C:13]([O-:16])(=[O:15])[CH3:14].[Na+]>C(O)(=O)C>[C:13]([O:16][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=[O:4])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 5880832-Chloro-1-(2,4-difluorophenyl)ethanone

Product 1

HCID 152530262-Acetoxy-2',4'-difluoroacetophenoneYield 75.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-chloro-2',4'-difluoroacetophenone (19.0 g) and anhydrous sodium acetate (16.4 g) in acetic acid (50 ml) was heated under reflux for 4 hours and then evaporated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with sodium bicarbonate solution and dried (Na2SO4). Evaporation of the solvent gave an oil which was triturated with hexane. The resulting solid was filtered off, washed with hexane and dried to give the title compound, (16.2 g), m.p. 54°-56°.

Workup

  1. temperatureunder reflux for 4 hours
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with sodium bicarbonate solution
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent
  8. customgave an oil which
  9. customwas triturated with hexane
  10. filtrationThe resulting solid was filtered off
  11. washwashed with hexane
  12. customdried

Sources & evidence

ORD record
ord-08a15c1c12a84f5cafd30c53157426ca
Source dataset
uspto-grants-1993_04
Patent number
US05206364

Reaction notes

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