反应详情

温度

0 °C

1,3,5-Tri-t-butylbenzene (150 g, 0.6 mol) was dissolved in 600 mL of carbon tetrachloride in a three-neck flask painted black to avoid light; The flask was equipped with an overhead stirrer, a thermometer, and an addition funnel under argon. Ferric chloride (3.0 g, 0.018 mol) was added and the solution was cooled to 0° C. A solution of bromine (120 g, 0.75 mol) dissolved in 200 mL of carbon tetrachloride was then added over a 2-hour period. The solution was stirred for an additional 1 hour at 0° C. and quenched with ice water. The layers were separated and the organics washed with 10% sodium hydroxide solution. The solution was then washed with salt brine and dried over magnesium sulfate. The solvent was removed under vacuum and the product was distilled through a 2-ft (60-cm) column under vacuum two times. The fractions boiling at 90°-110° C. at 0.4 mm Hg were combined and recrystallized from heptane to give 100 g of pure 3,5-di-t-butylbromobenzene (60% yield).

1. customThe flask was equipped with an overhead stirrer
2. additionwas then added over a 2-hour period
3. customquenched with ice water
4. customThe layers were separated
5. washthe organics washed with 10% sodium hydroxide solution
6. washThe solution was then washed with salt brine
7. dry with materialdried over magnesium sulfate
8. customThe solvent was removed under vacuum
9. distillationthe product was distilled through a 2-ft (60-cm) column under vacuum two times
10. customrecrystallized from heptane