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

HRID 426299Notes

Reaction equation

HRID 426299 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(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).

Workup

  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))

Sources & evidence

ORD record
ord-ebf77b56b0364d1491516879aa57c246
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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