반응 #955966

반응 방정식

tert-butyllithium

trimethyltin chloride

benzo[1,2-b:4,5-b′]dithiophene

→

solid

수율 88.4%

2,6-bis(trimethylstannyl)benzo[1,2-b:4,5-b′]dithiophene

수율 88.4%

용매

—

hexanes

tetrahydrofuran

반응 조건

후처리

1. 1
   기타A dry 1 L three-neck round bottom flask was flushed with N2
2. 2
   기타via deoxygenated syringe
3. 3
   기타via deoxygenated syringe
4. 4
   온도the solution was chilled to 0° C.
5. 5
   workup.STIRRINGstirring
6. 6
   workup.WAITwas continued for 5 minutes, at which
7. 7
   온도was cooled back to −78° C
8. 8
   workup.STIRRINGstirring
9. 9
   workup.WAITcontinued for 30 minutes at −76° C
10. 10
    기타The cooling bath was removed
11. 11
    온도to warm to ambient temperature
12. 12
    온도cool DI water (50 mL)
13. 13
    workup.ADDITIONwas slowly added to the reaction flask
14. 14
    workup.ADDITIONThen, the reaction mixture was poured into 300 mL of cool water
15. 15
    추출extracted with MTBE (300 mL) three times
16. 16
    세척The combined organic layer was washed with water two times
17. 17
    건조dried over anhydrous magnesium sulfate (MgSO4)
18. 18
    여과After the product was filtered
19. 19
    기타the solvent was removed by rotary evaporation
20. 20
    기타The crude product was purified by precipitation into methanol from a THF solution

실험 절차

A dry 1 L three-neck round bottom flask was flushed with N2 and was charged with benzo[1,2-b:4,5-b′]dithiophene (5.20 g, 26.3 mmol) and anhydrous tetrahydrofuran (THF) (300 mL, 0.01 M) via deoxygenated syringe. The reaction flask was cooled to −78° C. and a 1.3 M solution of tert-butyllithium in hexanes (53.0 mL, 68.8 mmol) was added dropwise via deoxygenated syringe. After 30 minutes of stirring at −78° C., the solution was chilled to 0° C. and stirring was continued for 5 minutes, at which point the reaction mixture was cooled back to −78° C. A 1 M solution of trimethyltin chloride (105 mL, 100 mmol) in hexanes was added to the reaction flask dropwise and stirring continued for 30 minutes at −76° C. The cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature. As the reaction was completed, cool DI water (50 mL) was slowly added to the reaction flask. Then, the reaction mixture was poured into 300 mL of cool water and extracted with MTBE (300 mL) three times. The combined organic layer was washed with water two times and dried over anhydrous magnesium sulfate (MgSO4). After the product was filtered, the solvent was removed by rotary evaporation. The crude product was purified by precipitation into methanol from a THF solution to yield white solid (12.0 g, 88%).

출처