Reaktion #2320133

Reaktionsgleichung

4-bromophenylboronic acid

2-bromo-5-methylpyridine

potassium carbonate

1,2-dimethoxyethane

→

2-(4-bromophenyl)-5-methylpyridine

Ausbeute 91.9%

Lösungsmittel

water

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturto reflux under nitrogen atmosphere for 18 hours
3. 3
   TemperaturAfter the reaction was cooled down
4. 4
   SonstigeThe mixture was separated in a separatory funnel
5. 5
   SonstigeThe organic phases were collected
6. 6
   Sonstigeevaporated
7. 7
   workup.DISTILLATIONThe mixture was distilled

Vorschrift

To a 500 mL round bottom flask, 4-bromophenylboronic acid (25.0 g, 0.125), 2-bromo-5-methylpyridine (20.0 g, 0.114 mol), palladium(0)tetrakistriphenylphosphine (4.0 g, 0.0035 mol), potassium carbonate (47.0 g, 0.34 mol.), 1,2-dimethoxyethane (120 mL) and water (120 mL.) were added. The mixture was heated to reflux under nitrogen atmosphere for 18 hours. After the reaction was cooled down, 100 mL of water and 150 mL of ethyl acetate were added. The mixture was separated in a separatory funnel. The organic phases were collected, combined and evaporated. The mixture was distilled using a kugelrohred (spelling?) to obtain 2-(4-bromophenyl)-5-methylpyridine (26.0 g) as a white solid that was further purified by recrystallization in hexanes.

Quelle