Allyl bromide → HCID 15128648, compound

Participants

Reaction Conditions

Reaction Steps

A solution of [2-(2-nitrophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (10 g, 25.81 mmol; see Example 15A) in 51 ml of dry dimethylformamide (0° C., argon) was treated with sodium hydride (6.19 g, 154.86 mmol of a 60% mineral oil dispersion); stirring at 0° C. was continued for 20 minutes. Allyl bromide* (11.17 ml, 129.05 mmol) was added and the reaction was carried out at room temperature for 1 hour, 10 minutes. The reaction was quenched by the slow addition of 1M hydrochloric acid (0° C. ice bath) followed by ethyl acetate. The aqueous layer was washed with ethyl acetate, the combined ethyl acetate layers were washed with 1M hydrochloric acid (3 times), saturated aqueous potassium carbonate solution (2 times), brine, dried over magnesium sulfate and evaporated in vacuo. The crude product was dissolved in dichloromethane and adsorbed onto Celite and filtered through a pad of silica gel (240-400 mesh, hexane, followed by 75/25 hexane/ethyl acetate). Evaporation in vacuo yielded 10.66 g of a viscous yellow-orange oil.

Provenance & Evidence