2-(Tributylstannyl)thiophene

Chemical Properties

Uses

Uses

Synthesis

1003-09-4

1461-22-9

54663-78-4

2-Bromothiophene (4.89 g, 30 mmol) and 60 mL of anhydrous tetrahydrofuran were added to a 250 mL three-necked flask with a device constant pressure dropping funnel. The system was evacuated and then displaced three times with argon to remove air. The reaction flask was placed in a cryostat reaction bath and cooled to -20 °C. Subsequently, a n-hexane solution of n-butyllithium (2.2 mol/L, 15 mL, 33 mmol) was slowly added dropwise under argon protection and the temperature was maintained at -20 °C for 1 h of reaction. Next, tributyltin chloride (8.95 mL, 33 mmol) was slowly added dropwise and the reaction was continued at -20 °C for 1 hour. Upon completion of the reaction, the reaction system was slowly brought to room temperature and stirred overnight. After the reaction was terminated, 150 mL of deionized water was added to the reaction flask and extracted three times with dichloromethane (80 mL x 3). The organic layers were combined and washed three times with saturated saline (100 mL x 3). The organic phase was dried overnight over anhydrous magnesium sulfate and filtered to remove the desiccant. The filtrate was concentrated by rotary evaporation and the residue was purified by silica gel column chromatography using a petroleum ether solution containing a small amount of triethylamine as eluent to give 11.08 g of the colorless liquid product 2-tributylmethylstannylthiophene in 90% yield.

References