Reaktion #70263

Reaktionsgleichung

2-chloro-3-iodo-5-nitropyridine

phenylboronic acid

DCM

Cs2CO3

→

2-chloro-5-nitro-3-phenylpyridine

Ausbeute 55.7%

Lösungsmittel

dioxane water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated
2. 2
   Extraktionthe crude mixture was extracted between water and ethyl acetate
3. 3
   SonstigeThe solid residue was purified by chromatography over SiO2 eluting with hexane/dichloromethane

Vorschrift

In a schlenck tube, a mixture of 2-chloro-3-iodo-5-nitropyridine (1.76 mmol, 0.5 g), phenylboronic acid (1.94 mmol, 0.24 g), PdCl2dppf.DCM (0.18 mmol, 0.1 g), Cs2CO3 (5.28 mmol, 1.7 g) in a dioxane/water 4:1 mixture (6.5 ml) was heated at 120° C. for 4 hours, under argon atmosphere. The solvent was evaporated and the crude mixture was extracted between water and ethyl acetate. The solid residue was purified by chromatography over SiO2 eluting with hexane/dichloromethane mixtures affording 2-chloro-5-nitro-3-phenylpyridine (0.23 g, yield 55%) of the expected product.

Quelle