Water → HCID 21249825, compound

HRID 1531637Notes

Reaction equation

HRID 1531637 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].C[O:15][C:16](=[O:25])[C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19](Cl)[N:18]=1.O>O1CCOCC1.[Cu](I)I>[Cl:23][C:21]1[CH:20]=[C:19]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[N:18]=[C:17]([C:16]([OH:25])=[O:15])[CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 18922464Methyl 4,6-dichloropyridine-2-carboxylate

Product 1

HCID 21249825HCID 21249825, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
125 °C

Procedure

3-(trifluoromethyl) phenol (3.15 g, 0.0019 mol) was dissolved in 50 ml of dried dioxane. Sodium hydride (0.8 g (ca. 60% in mineral oil), 0.0019×1.05 mol) was added to the obtained solution at room temperature. After completion of the foaming, a solution obtained by dissolving 4,6-dichloro picolinic acid methyl ester (4.0 g, 0.0019 mol) in 5 ml of dried dioxane, was dropped into the above solution. Successively, copper iodide (3.7 g, 0.0019×1.0 mol) was added to the obtained solution. The resultant mixture was heated and stirred at a temperature of 120 to 130° C. for 10 hours. Thereafter, the obtained reaction solution was cooled, mixed with 10 ml of water, and then filtered through a glass filter provided with High-flow Super Cell. The obtained filtrate was extracted with 100 ml of ethyl acetate two times, thereby separating an organic phase therefrom. The obtained organic phase was dried with sodium anhydride. After the dried organic phase was subjected to distillation to remove the solvent therefrom, the obtained distillation residues were purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. customAfter completion of the foaming, a solution obtained
  2. additionwas dropped into the above solution
  3. customThereafter, the obtained reaction solution
  4. temperaturewas cooled
  5. filtrationfiltered through a glass
  6. filtrationfilter
  7. customprovided with High-flow Super Cell
  8. extractionThe obtained filtrate was extracted with 100 ml of ethyl acetate two times
  9. customseparating an organic phase
  10. dry with materialThe obtained organic phase was dried with sodium anhydride
  11. distillationAfter the dried organic phase was subjected to distillation
  12. customto remove the solvent
  13. distillationthe obtained distillation residues
  14. customwere purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-446e427840214dd6ab2ef36f389d8093
Source dataset
uspto-grants-2001_03
Patent number
US06200933B1

Reaction notes

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