反应详情

温度

90 °C

5,5′-bis(tributylstannyl)-2,2′-bithiophene (2.16 g, 2.90 mmol) was dissolved in dry DMF (45 mL) and transferred via cannula to Pd(PPh3)4 (0.101 g, 0.087 mmol) in a Schlenk flask. 2-bromothiophene (1.14 g, 6.96 mmol) was added via syringe and the solution was degassed with nitrogen. Reaction was then heated to 90° C. for 18 hours. Reaction was quenched with water, extracted with chloroform (3×), and the combined organics washed with brine. Organics were dried with magnesium sulfate and concentrated by rotary evaporator yielding crude material as a waxy orange solid. The solid was recrystallized from boiling toluene and collected by filtration. Filtered solid was then redissolved in boiling chloroform and stirred with activated charcoal for 15 minutes. The charcoal was removed by filtering through celite and the chloroform removed by rotary evaporator to yield product as a yellow solid (0.676 g, 2.05 mmol, 70%). Characterization data matches literature. Z. H. Li, et al., Org. Lett. 9:3659-3662 (2007).

1. customthe solution was degassed with nitrogen
2. customReaction
3. customReaction
4. customwas quenched with water
5. extractionextracted with chloroform (3×)
6. washthe combined organics washed with brine
7. dry with materialOrganics were dried with magnesium sulfate
8. concentrationconcentrated by rotary evaporator
9. customyielding crude material as a waxy orange solid
10. customThe solid was recrystallized
11. filtrationcollected by filtration
12. filtrationFiltered solid
13. dissolutionwas then redissolved
14. customThe charcoal was removed
15. filtrationby filtering through celite
16. customthe chloroform removed by rotary evaporator