Ethyl Bromide → HCID 20470474, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 5 ml of dry THF and 0.3 ml of ethyl bromide were added to 2.92 g of magnesium turnings for Grignard reaction, and the mixture was stirred. Heat was generated and the temperature of the mixture rose. Then, a solution composed of 16.65 g of p-chloro-(2-methyl-2-propenyl)benzene and 2 ml of THF was added dropwise, and the temperature of the mixture was raised to 130° C. Some amount of THF was added, and the mixture was heated under reflux at 100° C. for 4 hours. After cooling, 60 ml of THF was added, and the resulting reaction mixture was added dropwise to a solution composed of 18.1 g of ethyl α-bromopropionate, 0.065 g of nickel chloride and 40 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, concentrated and distilled to give 11.3 g (yield 48.7%) of ethyl α-[p-(2-methyl-2-propenyl)phenyl]propionate having the following properties.

Provenance & Evidence