Reaktion #158256

Reaktionsgleichung

m-methoxy-phenylboronic acid

2,6-dichloropyridine

potassium carbonate

triphenylphosphine

→

2-chloro-6-(3-methoxyphenyl)pyridine

Lösungsmittel

water

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas prepared
2. 2
   SonstigeNitrogen was bubbled directly in the mixture for 20 minutes
3. 3
   workup.ADDITIONThen palladium acetate was added (0.44 g, 2.0 mmol)
4. 4
   SonstigeNitrogen was bubbled again in the mixture for another 10 minutes
5. 5
   TemperaturThe mixture was heated
6. 6
   Temperaturto reflux under nitrogen overnight
7. 7
   SonstigeThe organic layer was separated
8. 8
   Extraktionthe aqueous layer was extracted with dichloromethane
9. 9
   TrocknenThe combined organic layers were dried over magnesium sulfate
10. 10
    Filtrationfiltered
11. 11
    Sonstigeevaporated
12. 12
    SonstigeThe mixture was purified by silica column with up to 10% ethyl acetate in hexanes

Vorschrift

A mixture of m-methoxy-phenylboronic acid (10 g, 65.8 mmol), 2,6-dichloropyridine (9.7 g, 65.8 mmol), potassium carbonate (27.3 g, 197.4 mmol), triphenylphosphine (2.07 g, 7.9 mmol), dimethoxyethane 250 mL and water 80 mL was prepared. Nitrogen was bubbled directly in the mixture for 20 minutes. Then palladium acetate was added (0.44 g, 2.0 mmol). Nitrogen was bubbled again in the mixture for another 10 minutes. The mixture was heated to reflux under nitrogen overnight. The reaction mixture was cooled to room temperature. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and evaporated. The mixture was purified by silica column with up to 10% ethyl acetate in hexanes to gain 6.5 g colorless oil (45%).

Quelle