Ethyl Bromide → HCID 13241451, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of nitrogen, 0.1 g of ethyl bromide was added to a solution composed of 0.27 g of magnesium turnings for Grignard reaction, 1.67 g of p-chloro-(2-methyl-1-propenyl)benzene and 1 ml of THF. After the starting of the reaction, the mixture was heated to 115° C. THF was added little by little so as to maintain the temperature in the range of 110° to 120° C., and the mixture was maintained at this temperature for 4 hours. After cooling, 5 ml of THF was added. The resulting Grignard reagent solution was added dropwise to a solution composed of 1.81 g of ethyl α-bromopropionate, 0.013 g of nickel chloride and 4 ml of THF. After the addition, the mixture was stirred for 1 hour, and an aqueous solution of ammonium chloride was added. The mixture was extracted with diethyl ether. The ethereal extract was washed with an aqueous solution of sodium chloride, dried, and concentrated. The concentrate was purified by silica gel column chromatography to give 0.85 g (yield 36.6%) of ethyl α-[p-(2-methyl-1-propenyl)phenyl]propionate having the following NMR spectrum.

Provenance & Evidence