Potassium Carbonate → 1-(2-Fluoro-3-methoxy-6-nitrophenyl)propan-2-one

HRID 984853Notes

Reaction equation

HRID 984853 reaction equation
[F:1][C:2]1[C:7](F)=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH2:12][C:13](=[O:15])[CH3:14].[C:16](=O)([O-])[O-:17].[K+].[K+]>CO>[F:1][C:2]1[C:7]([O:17][CH3:16])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH2:12][C:13](=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 142688761-(2,3-Difluoro-6-nitrophenyl)propan-2-one

Product 1

HCID 220307431-(2-Fluoro-3-methoxy-6-nitrophenyl)propan-2-oneYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(2,3-difluoro-6-nitrophenyl)-propan-2-one (183 g) and potassium carbonate (100 g) in methanol (1 L) was heated at reflux for 3 h. The reaction mixture was then cooled and concentrated in vacuo to remove most of the methanol. The residue was diluted with ethyl acetate (1 L), filtered and washed with water. The separated aqueous layer was neutralized with 2N HCl and extracted with ethyl acetate (2×500 mL). The combined organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo to give a brown solid. The solid was triturated with diethyl ether and filtered to provide 1-(2-fluoro-3-methoxy-6-nitrophenyl)-propan-2-one (121 g, 71%) as a yellow solid. LC/MS; (M+H)+=228.2.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureThe reaction mixture was then cooled
  4. concentrationconcentrated in vacuo
  5. customto remove most of the methanol
  6. additionThe residue was diluted with ethyl acetate (1 L)
  7. filtrationfiltered
  8. washwashed with water
  9. extractionextracted with ethyl acetate (2×500 mL)
  10. washThe combined organic layer was washed with brine
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated in vacuo
  13. customto give a brown solid
  14. customThe solid was triturated with diethyl ether
  15. filtrationfiltered

Sources & evidence

ORD record
ord-5b1368bfe72e488fb70c5e9bcd0e24e6
Source dataset
uspto-grants-2005_03
Patent number
US06869952B2

Reaction notes

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