Trimethyltin chloride → HCID 58261082, compound

Temperature

-78 °C

A dry 250-mL three-neck round bottom flask was flushed with N2 and was charged with 4,8-dimethylbenzo[1,2-b:4,5-b′]dithiophene (1.02 g, 4.70 mmol) and anhydrous tetrahydrofuran (THF) (75.0 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 (9.00 mL, 23.0 mmol) was added drop-wise 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 (19.0 mL, 37.0 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 (10 mL) was slowly added to the reaction flask. Then, the reaction mixture was poured into 50 mL of cool water and extracted with MTBE (100 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 (1.90 g, 74%).

1. customA dry 250-mL three-neck round bottom flask was flushed with N2
2. customvia deoxygenated syringe
3. customvia deoxygenated syringe
4. temperaturethe solution was chilled to 0° C.
5. stirringstirring
6. waitwas continued for 5 minutes, at which
7. temperaturewas cooled back to −78° C
8. stirringstirring
9. waitcontinued for 30 minutes at −76° C
10. customThe cooling bath was removed
11. temperatureto warm to ambient temperature
12. temperaturecool DI water (10 mL)
13. additionwas slowly added to the reaction flask
14. additionThen, the reaction mixture was poured into 50 mL of cool water
15. extractionextracted with MTBE (100 mL) three times
16. washThe combined organic layer was washed with water two times
17. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
18. filtrationAfter the product was filtered
19. customthe solvent was removed by rotary evaporation
20. customThe crude product was purified by precipitation into methanol from a THF solution

ORD record

ord-b91112e020174caab394614a1d24eecd

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08968885B2