Reaktion #70258

Reaktionsgleichung

3-iodo-5-nitropyridin-2-ol

phenylboronic acid

DCM

Cs2CO3

→

expected product

5-Nitro-3-phenylpyridin-2-ol

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 organic phase was evaporated
4. 4
   Filtrationthat was filtered off
5. 5
   Sonstigedried under vacuum overnight
6. 6
   Sonstigeaffording

Vorschrift

In a schlenck tube, a mixture of 3-iodo-5-nitropyridin-2-ol (7.52 mmol, 2 g), phenylboronic acid (8.28 mmol, 1.01 g), PdCl2dppf.DCM (0.75 mmol, 0.6 g), Cs2CO3 (22.56 mmol, 7.4 g) in a dioxane/water 4:1 mixture (26 ml) was heated at 100° C. for 4 hours, under argon atmosphere. The solvent was evaporated and the crude mixture was extracted between water and ethyl acetate. The organic phase was evaporated and the crude was suspended in methanol affording a solid that was filtered off and dried under vacuum overnight affording 1.2 g (74% of yield) of the expected product.

Quelle