Trimethyltin chloride → 2-Bromo-1-trimethylstannylcyclopentadiene

関与物質

反応条件

反応手順

n-Butyllithium, 1.6M in hexanes, (58 mL, 92.0 mmol) in THF (50 mL) was cooled under nitrogen to −75° C. 1,2-Dibromocyclopentene (10.00 g, 44.3 mmol) in dry THF (10 mL) was added dropwise over ˜10 minutes. The mixture was stirred at −75° C. for a further 20 minutes and then allowed to reach 0° C. The reaction mixture was then re-cooled to −75° C. and trimethyltin chloride (8.85 g, 44.3 mmol) in THF (30 mL) was added, under nitrogen, over ˜10 minutes. After stirring at −75° C. for 30 minutes the reaction was allowed to reach room temperature and then stirred for 2 hours. The reaction mixture was then evaporated down to an oil and partitioned between brine and dichloromethane (100/200 mL). After shaking thoroughly, the organic layer was dried (magnesium sulphate), filtered and evaporated to give an oil. (13.15 g, ˜80% pure).

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