Iodine → Tributyl(2-methylprop-1-en-1-yl)stannane

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A suspension of magnesium (2.64 g, 110 mmol) in dry tetrahydrofuran (60 mL) was treated with a small amount of iodine and then 1-bromo-2-methylpropene (13.5 g, 100 mmol) in tetrahydrofuran (30 mL) was added in several portions. The mixture was heated under reflux for 3 min. The mixture was cooled to 25° C. and then treated with iodomethane (0.2 mL, 3.0 mmol). The reaction mixture was stirred at 25° C. for 30 min and then heated under reflux for 2 h until all the magnesium was consumed. The mixture was cooled to 25° C. then treated with a solution of tributyltin chloride (27 mL, 100 mmol) in tetrahydrofuran (30 mL). The mixture was heated under reflux for 19 h and then cooled to 25° C. The solution was extracted with diethyl ether and a saturated aqueous ammonium chloride solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford isobutenyltri-n-butyltin (31.95 g) as a crude oil. The 1H-NMR data of the crude oil indicated 58% purity of the desired isobutenyltri-n-butyltin.

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