(3,5-Dichloro-2,6-difluoropyridin-4-yl)methyl benzoate → (2,6-Difluoropyridin-4-yl)methyl benzoate

HRID 426299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426299
[C:1]([O:9][CH2:10][C:11]1[C:16](Cl)=[C:15]([F:18])[N:14]=[C:13]([F:19])[C:12]=1Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)C>[C:1]([O:9][CH2:10][C:11]1[CH:16]=[C:15]([F:18])[N:14]=[C:13]([F:19])[CH:12]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 59184839(3,5-Dichloro-2,6-difluoropyridin-4-yl)methyl benzoate

Produkt 1

HCID 59184643(2,6-Difluoropyridin-4-yl)methyl benzoateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

(3,5-dichloro-2,6-difluoropyridin-4-yl)methyl benzoate (19.6 g, 61.6 mmol), anhydrous ethanol (150 ml), and 10% palladium on carbon (3 g) were placed into a 500 mL bottle. The mixture was hydrogenated under hydrogen atmosphere (50 psi) for 1.5 hr. The reaction mixture was filtered through celite pad and the pad was washed with ethanol. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:4)) to afford 9.15 g (61%) of (2,6-difluoropyridin-4-yl)methyl benzoate as a white solid. m.p. 83-84° C. 1H NMR (200 MHz, CDCl3) δ 5.42 (2H, s), 6.87 (2H, s), 7.45-7.67 (3H, m), 8.08-8.13 (2H, m).

Aufarbeitung

  1. customfor 1.5 hr
  2. filtrationThe reaction mixture was filtered through celite pad
  3. washthe pad was washed with ethanol
  4. customThe combined filtrate was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:4))

Quellen und Nachweise

ORD-Eintrag
ord-ebf77b56b0364d1491516879aa57c246
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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