Diethyl Ether → Benzoic acid 2-fluoro-pyridin-4-ylmethyl ester

HRID 426114

Reaktionsgleichung

Reaktionsgleichung von HRID 426114
Br[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([F:9])[CH:4]=1.[C:10]([O-:18])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Na+].CCOCC>CN(C=O)C>[F:9][C:5]1[CH:4]=[C:3]([CH2:2][O:18][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 517055Sodium BenzoateHCID 139851684-Bromomethyl-2-fluoropyridine

Produkt 1

HCID 59184859Benzoic acid 2-fluoro-pyridin-4-ylmethyl esterAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The mixture of 4-Bromomethyl-2-fluoro-pyridine (35) (4.85 g, 25.5 mmol) and sodium benzoate (5.51 g, 38.25 mmol) in DMF (60 ml) was stirred at room temperature for 3 hr. Ether was then added and the mixture was washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ether:hexane (1:4)) to afford 4.68 g (79%) of a colorless oil; 1H NMR (200 MHz, CDCl3) δ: 5.41 (2H, s), 7.11 (1H, m), 7.45-7.66 (3H, m), 8.08-8.12 (2H, m), 8.23 (1H, d, J=5.4 Hz); m/z (EI): 231 (M+).

Aufarbeitung

  1. washthe mixture was washed with water
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:4))

Quellen und Nachweise

ORD-Eintrag
ord-11432487aa5446ddbfa3e0ab506a8082
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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