반응 #450365

반응 방정식

2-bromo-5-methylpyridine

phenylboronic acid

barium hydroxide

DME

→

title compound

2-Phenyl-5-methylpyridine

용매

water

반응 조건

후처리

1. 1
   기타was purged with dry argon
2. 2
   기타The solvents were evaporated in vacuo
3. 3
   기타the residue partitioned between EtOAc and water
4. 4
   추출The aqueous extract
5. 5
   기타was separated
6. 6
   추출extracted with EtOAc
7. 7
   세척washed with NaHCO3 and 5% aq. Na2S2O3
8. 8
   건조dried (Na2SO4)
9. 9
   여과filtered
10. 10
    기타the solvent evaporated in vacuo
11. 11
    기타The residue was purified by chromatography (Silica gel, CH2Cl2)

실험 절차

A mixture of 2-bromo-5-methylpyridine (2.00 g, 11.63 mmol), phenylboronic acid (1.56 g, 12.79 mmol), barium hydroxide (5.50 g, 17.4 mmol), DME (80 mL) and water (15 mL) was purged with dry argon. Tetrakis(triphenylphosphine)palladium(0) (672 mg, 0.58 mmol) was added, and the resultant solution was stirred at 80° C. for 4 hours. The solvents were evaporated in vacuo, and the residue partitioned between EtOAc and water and acidified with 1M aq. HCl. The aqueous extract was separated, and extracted with EtOAc. The organic extracts were combined, washed with NaHCO3 and 5% aq. Na2S2O3, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The residue was purified by chromatography (Silica gel, CH2Cl2) to afford the title compound.

출처