반응 #2487418

반응 방정식

2-([1,1′-Biphenyl]-3-yl)-5-bromo-4-methylpyridine

2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane

potassium phosphate tribasic monohydrate

toluene

→

product

수율 87.0%

2-([1,1′-biphenyl]-3-yl)-4,5-dimethylpyridine

수율 87.0%

용매

water

반응 조건

후처리

1. 1
   기타The reaction mixture was degassed with nitrogen for 20 minutes
2. 2
   온도heated
3. 3
   온도to reflux for 24 h
4. 4
   온도After cooling
5. 5
   기타the organic layer was separated
6. 6
   추출the aqueous layer extracted 3×50 mL with dichloromethane
7. 7
   건조dried over sodium sulfate
8. 8
   기타evaporated
9. 9
   기타The crude product was chromatographed on silica gel with 5% dichloromethane in hexane

실험 절차

2-([1,1′-Biphenyl]-3-yl)-5-bromo-4-methylpyridine 11.5 g (35.5 mmol), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (5.57 g, 44.3 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-3-yl)phosphine (1.2 g, 2.84 mmol), Pd2dba3 (0.650 g, 0.709 mmol) and potassium phosphate tribasic monohydrate, 250 mL toluene and 25 mL of water were placed in flask under nitrogen. The reaction mixture was degassed with nitrogen for 20 minutes and heated to reflux for 24 h. After cooling, the organic layer was separated and the aqueous layer extracted 3×50 mL with dichloromethane, dried over sodium sulfate and evaporated. The crude product was chromatographed on silica gel with 5% dichloromethane in hexane to give 8.0 g (87%) of the product. The product was confirmed by NMR and GC/MS.

출처