3,5-Dimethoxybenzyl Bromide → 3-(3,5-Dimethoxyphenyl)-1-propene

Participants

Reaction Steps

To a suspension of 308 mg (1.62 mmol, 25 mol %) of copper (I) iodide in 30 mL of THF was added dropwise vinylmagnesium bromide as a 1 M solution in THF at −50° C. After stirring for 10 min, a solution of 1.5 g (6.49 mmol) of 3,5-dimethoxybenzyl bromide in 8 mL of THF was added, and the resulting solution was stirred at −30° C. for 1 h and then was warmed to room temperature. The reaction mixture was quenched by the slow addition of 20 mL of water. After stirring for 5 min, the layers were separated and the aqueous layer was extracted twice with 20-mL portions of ethyl acetate. The combined organic fractions were dried (Na2SO4), filtered through a plug of silica gel (eluted with ethyl acetate) and concentrated in vacuo to afford 1.2 g (100%) of product as a yellow oil.

Provenance & Evidence