Dichlorodimethylsilane → HCID 22902837, compound

Participants

Reaction Steps

A 100 mL three-neck flask was equipped with an addition funnel, condenser, and stir bar. The flask was flame dried, flushed with argon and charged with magnesium (1.04 g, 42.8 mmol) and 5 mL of dry ether. A few drops of 1,2-dibromoethane was added to activate the magnesium and caused the ether to reflux. p-Dibromobenzene (10 g, 42.4 mmol) in 40 mL of ether was added dropwise at such a rate as to maintain reflux. After complete addition, the reaction mixture was heated to maintain reflux for an additional five hours. Upon cooling to room temperature copper cyanide (0.1 g, 1.1 mmol) was introduced. The reaction mixture was then cooled to 0 C. and dichlorodimethylsilane (2.55 g, 19.8 mmol) was added dropwise through the addition funnel causing the reaction to warm slightly. The reaction mixture was stirred overnight at room temperature. The product mixture was poured over ice and the organic layer was separated and dried over anhydrous sodium sulfate. The ether was removed by vacuum and a yellow oily solid was recovered. The crude product (5c) was fractionally sublimed under full vacuum. The first fraction contained non-reacted dibromobenzene and 2.6 g (36% yield) of 5c was collected for the second fraction. 1 H NMR (in CDCl3): d, 7.47 ppm 4H; d, 7.32 ppm 4H; s, 0.51 ppm 6H.

Provenance & Evidence