Chlorotrimethylsilane → HCID 67905434, compound

Participants

Reaction Conditions

Reaction Steps

700 mg of 1,2-dibromoethane are added to 2.3 g of zinc powder in 20 ml of THF (tetrahydrofuran). Refluxing is carried out until evolution of gas has ended, the mixture is allowed to cool to room temperature (20° C.) and 0.2 ml of trimethylchlorosilane is added. A solution of 10 g (35 mmol) of methyl α-(2-bromomethylphenyl)-β-methoxyacrylate in 40 ml of THF is added dropwise to this solution at 0° C. and stirring is continued for 3 hours at 5° C. Thereafter, the mixture is cooled to -78° C. and a solution of 3.2 g of copper cyanide and 3 g of lithium chloride in 40 ml of THF is added. The mixture is allowed to thaw for 5 minutes at -20° C. and is again cooled to -78° C., and a solution of 6.1 g of 2-chlorobenzoyl chloride in 20 ml of THF is added dropwise. Stirring is carried out overnight at room temperature. The reaction mixture is poured onto water and extracted with ethyl acetate, and the organic phase is dried and evaporated down. Chromatography over silica gel using hexane/ethyl acetate gives 4.1 g of compound No. 5 (Table 2) as a colorless solid of melting point 70°-75° C. Yield: 35%.

Provenance & Evidence