Reaktion #2320125

Reaktionsgleichung

2-Bromo-5-methylpyridine

3-bromophenylboronic acid

triphenylphosphine

potassium carbonate

→

2-(3-bromophenyl)-5-methylpyridine

Ausbeute 68.1%

Lösungsmittel

ethyl acetate

water

ethylene glycol dimethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with a temperature probe
2. 2
   Temperaturreflux condenser, and a magnetic stir bar
3. 3
   TemperaturThe solution was heated
4. 4
   Temperaturat reflux under nitrogen for 16 hr
5. 5
   SonstigeThe cooled reaction mixture
6. 6
   Sonstigewas then placed in a separatory funnel
7. 7
   ExtraktionThe organic layer was extracted twice with a saturated solution of sodium chloride
8. 8
   Trocknendried over magnesium sulfate
9. 9
   Sonstigeevaporated to dryness
10. 10
    workup.DISTILLATIONAfter the excess 2-bromo-5-methylpyridine was distilled off in vacuo at 110° C.
11. 11
    workup.DISTILLATIONthe 2-(3-bromophenyl)-5-methylpyridine was distilled at 200° C.
12. 12
    Sonstigeto give 30.1 g (68.1% yield) of a slightly orange liquid, which
13. 13
    Sonstigewas used for the next step without further purification

Vorschrift

2-Bromo-5-methylpyridine (46.1 g, 267 mmol), 3-bromophenylboronic acid (35.8 g, 178 mmol), palladium(II) acetate (1.00 g, 4.4 mmol), triphenylphosphine (4.67 g, 17.8 mmol), and potassium carbonate (67.8 g, 491 mmol) were mixed with 370 mL of ethylene glycol dimethyl ether and 245 mL of water in a 1000 mL round bottom flask equipped with a temperature probe, reflux condenser, and a magnetic stir bar. The solution was heated at reflux under nitrogen for 16 hr. The cooled reaction mixture was then placed in a separatory funnel, and 100 mL of ethyl acetate was added. The aqueous layer was discarded. The organic layer was extracted twice with a saturated solution of sodium chloride, dried over magnesium sulfate, and evaporated to dryness. After the excess 2-bromo-5-methylpyridine was distilled off in vacuo at 110° C., the 2-(3-bromophenyl)-5-methylpyridine was distilled at 200° C. to give 30.1 g (68.1% yield) of a slightly orange liquid, which was used for the next step without further purification.

Quelle