반응 #1609888

반응 방정식

2-bromo-5-methylpyridine

phenylboronic acid

potassium phosphate tribasic

toluene

→

desired product

수율 92.0%

2-phenyl-5-methylpyridine

수율 92.0%

용매

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타Nitrogen was bubbled for another 15 min
3. 3
   온도the reaction mixture was heated
4. 4
   온도to reflux for 16 h under nitrogen
5. 5
   온도The mixture was cooled
6. 6
   기타the organic layer was separated from the aqueous layer
7. 7
   세척The organic layers are washed with saturated brine solution
8. 8
   건조dried over magnesium sulfate
9. 9
   여과filtered
10. 10
    기타the solvent removed under vacuum
11. 11
    기타to give an off-white solid as the crude
12. 12
    기타The crude was purified by column chromatography

실험 절차

2-bromo-5-methylpyridine (11.25 g, 65.39 mmol), phenylboronic acid (9.5 g, 78.47 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.0 g, 2.61 mmol), and potassium phosphate tribasic (45 g, 196.17 mmol), 250 mL of toluene and 25 mL of water were placed in a 500 mL round-bottom flask. Nitrogen was bubbled directly into the mixture for 30 min after which tris(dibenzylideneacetone) dipalladium(0) (598 mg, 0.653 mmol) was added. Nitrogen was bubbled for another 15 min then the reaction mixture was heated to reflux for 16 h under nitrogen. The mixture was cooled and the organic layer was separated from the aqueous layer. The organic layers are washed with saturated brine solution, dried over magnesium sulfate, filtered, and the solvent removed under vacuum to give an off-white solid as the crude. The crude was purified by column chromatography using silica gel as the stationary phase and 5%-10% ethyl acetate in hexanes as the mobile phase. 10.11 g of desired product was obtained after purification (92% yield).

출처