4-Bromoanisole → HCID 57825023, compound

Participants

Reaction Steps

4-Bromoanisole (2.2 mL, 0.017 mol) in diethyl ether (10 mL) was added to a mixture of magnesium turnings (0.5 g, 0.02 mol) in diethyl ether (5 mL), at room temperature. The resulting mixture was heated to reflux for 1 h. The mixture was then cooled to room temperature. A solution of 3-bromoacetophenone (3.4 g, 0.017 mol) in diethyl ether was then added dropwise causing a gentle reflux. After 3 h heating to reflux the reaction mixture was examined by LC-MS which showed complete conversion to the desired product. The mixture was quenched with 1 N HCL solution (20 mL). Ethyl acetate (20 mL) was added and the aqueous phase was separated. The aqueous phase was then extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness under vacuum. The crude was then dissolved in toluene (10 mL) and a catalytic amount of p-toluene sulfonic acid (30 mg) was added and refluxed for 3 h. The solvent was removed and the crude residue was purified by column chromatography (cyclohexane) to afford the title compound as a colourless oil (3.7 g, 74%).

Provenance & Evidence