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

HRID 1938158Notes

Reaction equation

HRID 1938158 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+]>N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.CN(C=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

5

Reactant 2

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

Product 1

HCID 152530262-Acetoxy-2',4'-difluoroacetophenoneYield 92.2%

Reagents, catalysts & solvents 2

HCID 1859152-NaphthylalanineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Add 191 g of 2-chloro-2',4'-difluoroacetophenone (Aldrich Chemical Co.) to a mixture of 246 g of sodium acetate, 3 g of Nal, and 3L of DMF. Stir the mixture at 20° C. for 18 hr. then concentrate it to 1L. Pour the residue into 6L of cold dilute aqueous HCl and extract with EtOAc. Wash the extract with brine, dry it over anhydrous Na2SO4, filter the so-formed mixture, and evaporate the filtrate to leave a residue. Chromatograph the residue on silica gel, eluting with CH2Cl-2-hexane to obtain 198 g of the title compound. ##STR103##

Workup

  1. concentrationthen concentrate it to 1L
  2. additionPour the residue into 6L of cold dilute aqueous HCl
  3. extractionextract with EtOAc
  4. washWash the
  5. extractionextract with brine
  6. dry with materialdry it over anhydrous Na2SO4
  7. filtrationfilter the so-formed mixture
  8. customevaporate the filtrate
  9. customto leave a residue
  10. washChromatograph the residue on silica gel, eluting with CH2Cl-2-hexane

Sources & evidence

ORD record
ord-2e3392d773f04e7e88dd7a98b49de6a2
Source dataset
uspto-grants-1997_12
Patent number
US05693626

Reaction notes

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