反应详情

To a solution of 3-(p-methoxyphenyl)-1-propanol (16.6 g; 0.1 mol) in 250 ml of toluene, cooled to 0° C., was added dropwise 26 ml of phosphorus tribromide (0.27 mol). Following completion of the addition, the reaction was stirred at room temperature for 1 hour, then refluxed for an additional hour. The reaction was cooled and poured onto ice, the layers were separated, and the organic phase washed with saturated sodium bicarbonate (3×) and brine (3×). The crude material obtained upon drying and evaporation of the solvent was chromatographed, eluting with 10% EtOAc/hexane, to obtain 14 g (61%) of 3-(p-methoxyphenyl)-1-propylbromide.

1. additioncompletion of the addition
2. temperaturerefluxed for an additional hour
3. temperatureThe reaction was cooled
4. additionpoured onto ice
5. customthe layers were separated
6. washthe organic phase washed with saturated sodium bicarbonate (3×) and brine (3×)
7. customThe crude material obtained
8. customupon drying
9. customevaporation of the solvent
10. customwas chromatographed
11. washeluting with 10% EtOAc/hexane