반응 #44322

반응 방정식

hydrochloric acid

2-bromopyridine

(4-methoxyphenyl)magnesium bromide

4-bromoanisole

magnesium

→

2-(4-methoxy-phenyl)pyridine

용매

tetrahydrofuran

THF

반응 조건

후처리

1. 1
   온도the mixture was refluxed for 1 hour
2. 2
   세척the reaction mixture was washed with chloroform
3. 3
   추출the objective compound was extracted with chloroform
4. 4
   workup.DISTILLATIONthe organic layer was distilled off under reduced pressure
5. 5
   기타immediately solidified at room temperature

실험 절차

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.

출처