Iodine → Trimethyl-(4-prop-1-en-2-ylphenyl)silane

Participants

Reaction Conditions

Reaction Steps

Placing 2 g (83 mmol) of dry magnesium into a 250 mL flask equipped with a condenser, a dropping funnel and a magnetic stirrer, the reaction was carried out in a nitrogen atmosphere. The magnesium was initially activated by adding 1 mL of p-chloro-methylstyrene (Aldrich, Germany) with 0.5 g iodine in 5 mL THF at 50° C. for a period of 30 minutes. Into the mixture a solution of 11 g (72 mmol) of p-chloro-α-methylstyrene in 50 mL THF was dropped over a period of 12 hours under reflux. The reaction mixture was cooled to 40° C., then 7.8 g (72 mmol) of chlorotrimethylsilane (Fluka, Japan) in 30 mL of THF were added dropwise and reacted for 24 hours. After the reaction was completed, a large amount of water was added and the reaction mixture was extracted with ether. The ether layer was dried over magnesium sulfate, and distilled under reduced pressure, bp 66°-67° C./2 mmHg. Yield, 56%. The colorless liquid crude product was purified by column chromatography, which was performed on silica gel using n-hexane as an eluent. The product was identified by IR and 1H-NMR spectroscopy.

Provenance & Evidence