Thionyl Chloride → (5-Chloromethyl-pyridin-3-yl)-(4-fluoro-phenyl)-methanone
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([CH2:16]O)[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O>C(#N)C>[Cl:20][CH2:16][C:14]1[CH:15]=[C:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:9])[CH:11]=[N:12][CH:13]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of (4-fluoro-phenyl)-(5-hydroxymethyl-pyridin-3-yl)-methanone (1I) (410 mg, 1.8 mmol) in 25 mL of acetonitrile at 0° C., is added thionyl chloride (0.65 mL, 8.9 mmol) drop wise. After being stirred at room temperature for 2 hours, the reaction mixture is concentrated to remove most of thionyl chloride and acetonitrile. The residue is dissolved in 30 mL of CH2Cl2 and basified by saturated sodium bicarbonate to PH˜8.0. The organic layer is dried over sodium sulfate and concentrated to give (5-chloromethyl-pyridin-3-yl)-(4-fluoro-phenyl)-methanone (1J) (390 mg, yield 87%) as light yellow waxy solid. MS (ESI) m/e 250 (M+H+).