反应详情

To a 250 mL 3-neck round bottom flask was added 2,6-diisopropylaniline (2.365 g, 13.34 mmol) and 70 mL toluene. The solution was cooled in an ice bath under nitrogen and trimethylaluminum (2.0 M in toluene, 9.34 mL, 18.68 mmol) was added dropwise via dropping funnel. The reaction mixture was stirred at room temperature for 2 hours. Next, 3-bromo-5-methylbenzonitrile (3.4 g, 17.34 mmol) in 30 mL toluene was added and the reaction mixture was heated to 70° C. overnight under nitrogen. The reaction mixture was cooled in an ice bath and was poured onto a stirring slurry of silica gel in 2:1 dichloromethane/methanol (v/v). The silica gel was filtered off and washed with dichloromethane and methanol. The filtrate was evaporated leaving a solid. Hexane was added to the solvent and the solid was filtered off and washed with hexane (2.92 g, 59%).

1. temperatureThe solution was cooled in an ice bath under nitrogen
2. temperaturethe reaction mixture was heated to 70° C. overnight under nitrogen
3. temperatureThe reaction mixture was cooled in an ice bath
4. filtrationThe silica gel was filtered off
5. washwashed with dichloromethane and methanol
6. customThe filtrate was evaporated
7. customleaving a solid
8. filtrationthe solid was filtered off
9. washwashed with hexane (2.92 g, 59%)