Reaktion #44322

Reaktionsgleichung

hydrochloric acid

2-bromopyridine

(4-methoxyphenyl)magnesium bromide

4-bromoanisole

magnesium

→

2-(4-methoxy-phenyl)pyridine

Lösungsmittel

tetrahydrofuran

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed for 1 hour
2. 2
   Waschenthe reaction mixture was washed with chloroform
3. 3
   Extraktionthe objective compound was extracted with chloroform
4. 4
   workup.DISTILLATIONthe organic layer was distilled off under reduced pressure
5. 5
   Sonstigeimmediately solidified at room temperature

Vorschrift

That is, as shown in the Reaction Scheme below, (4-methoxyphenyl)magnesium bromide was synthesized from 22.4 g (120 mmol) of 4-bromoanisole by a conventional method by using 3.4 g of magnesium (Mg) in dry tetrahydrofuran (THF) under argon stream and added slowly into a solution of 15.8 g (100 mmol) of 2-bromopyridine and 1.8 g of (1,2-bis(diphenylphosphino)ethane)dichloronickel (II) (Ni(dppe)Cl2) in dry THF and the mixture was refluxed for 1 hour. After adding 250 ml of an aqueous solution of 5% hydrochloric acid to the reaction mixture, the reaction mixture was washed with chloroform. The water layer was neutralized with an aqueous solution of sodium hydrogen carbonate and the objective compound was extracted with chloroform and the organic layer was distilled off under reduced pressure. The distillate immediately solidified at room temperature to obtain 15.1 g (81.5 mmol) of 2-(4-methoxy-phenyl)pyridine (4-MeO-PPy) as white solid. Identification was performed by elementary analysis of C, H and N and 1H-NMR.

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