1,2-Dibromoethane → HCID 15332486, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 7.9 g (0.329 mole) of magnesium metal and 0.5 mL of 1,2-dibromoethane in 150 mL of diethyl ether was added dropwise a solution of 50 g (0.271 mole) of (chloromethyl)dimethylphenylsilane in 100 mL of diethyl ether. The addition required 30 minutes. Upon completion of addition, the resultant solution was transferred using a cannula to a flask containing 15.5 g (0.108 mole) of copper(I) bromide which was under a nitrogen atmosphere and was cooled in a dry ice/acetone bath. To this flask was added dropwise a solution 10.8 g (0.108 mole) of ethyl acrylate in 50 mL of diethyl ether. The addition required 40 minutes. Upon completion of addition, the reaction mixture was allowed to warm to -10° C. It was then diluted with 400 mL of diethyl ether, and a solution of 14.2 g of ammonium chloride in 40 mL of water was added dropwise while maintaining the temperature at -10° C. to 0° C. Upon completion of addition, the reaction mixture was filtered, and the solvent was evaporated under reduced pressure, leaving a residue. This residue was passed through a column of silica gel, eluting with diethyl ether/petroleum ether (5:95). The product-containing fractions were combined, and the solvent was evaporated, yielding 12.95 g of ethyl 5-methyl-5-phenyl-5-silahexanoate as an oil.

Provenance & Evidence