Chlorotrimethylsilane → Phenyltrimethylsilane

Participants

Reaction Steps

A toluene (5 g) solution containing 0.87 g (8.60 mmol, 2 mol %) of diisopropylamine was added to phenyl sodium, which had been prepared by reacting 20.0 g (0.870 mol) of sodium dispersion and 48.0 g (0.426 mol) of chlorobenzene in 160 g of tolunene, at room temperature, and then the reaction mixture was stirred for 2 hours. To the resultant greenish brown slurry, 46.3 g (0.426 mol) of trimethylchlorosilane was added, dropwise, keeping the reaction temperature in the range of from 15 to 20° C., and then the reaction mixture was subjected to hydrolysis with 100 ml of water. After the separated organic layer was washed with water three times, the thus-obtained organic solution was subjected to gas chromatography analysis. As a result, it was found that benzyltrimethylsilane was produced, at the yield of 98.5%, while the yield of phenyltrimethylsilane was not more than 0.5%. This fact indicates that phenyl sodium was almost quantitatively converted to benzyl sodium. Further, a solvent was distilled off from the obtained organic layer, and then the remaining slightly yellowish oil was distilled under reduced pressure, to give 65.5 g of benzyltrimethylsilane (0.399 mol, 93.7%, b.p. 120 to 122° C./100 mmHg).

Provenance & Evidence