Synthesis
The general procedure for the synthesis of 3-(3-methoxyphenyl)-1-propene from m-bromoanisole and 3-bromo-1-propene was as follows:
1. Preparation of the intermediate 1-methyl-3-methoxybenzene (IIa): 3-bromoanisole (40 g, 0.2138 mol) was dissolved in anhydrous THF (220 mL) and added slowly and dropwise to a solution that had been pre-activated (by addition of a small amount of iodine and briefly heated to initiate the reaction) with magnesium (7.9 g, 0.328 mol) in anhydrous THF (20 mL). After 1 hr of reaction, when the solution was gray and most of the magnesium was dissolved, allyl bromide (28.4 mL, 0.328 mol) was added. The reaction was continued for 3 hours and then quenched with saturated NH4Cl solution. The organic layer was extracted with ether and dried over anhydrous Na2SO4, followed by evaporation of the solvent. The crude product was purified by column chromatography on silica gel (230-400 mesh) using a petroleum ether solution of 3-4% ethyl acetate as eluent to afford the allyl compound as a yellow viscous liquid (24 g, 76% yield).
References
[1] Journal of Organic Chemistry, 2013, vol. 78, # 19, p. 9772 - 9780
[2] Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2638 - 2643
[3] Patent: WO2008/135488, 2008, A1. Location in patent: Page/Page column 43
[4] Tetrahedron, 2010, vol. 66, # 34, p. 6965 - 6976
[5] Chemical and Pharmaceutical Bulletin, 2018, vol. 66, # 7, p. 741 - 747
