反应详情

Under an atmosphere of argon, 9-bromo-10-(4-bromophenyl)-anthracene (3.0 g, 7.3 mmole), 4-(2,2-diphenylvinyl)phenylboronic acid (6.6 g, 22 mmole, 3 eq) and tetrakis(triphenylphosphine)palladium(0) (0.34 g, 0.29 mmole, 2% Pd) were suspended into toluene (60 ml). To the obtained suspension, a 2 M aqueous solution of sodium carbonate (7.0 g, 66 mmole, 3 eq/35 ml) was added and the resultant mixture was heated under refluxing for 10 hours. The reaction mixture was filtered and washed with toluene, water and methanol and a gray solid (1.4 g, the first crop, 25%) was obtained. From the filtrate, the organic layer was separated, washed with a saturated aqueous solution of sodium chloride and dried with magnesium sulfate. The solvent was removed by distillation and a deep brown oil was obtained. When the obtained oil was dissolved in dichloromethane, crystals were formed soon. The formed crystals were separated by filtration and washed with a mixed solvent composed of hexane and dichloromethane and a white solid (3.3 g, the second crop, 59%) was obtained. The obtained crude crystals (3.5 g) were suspended in boiling toluene (40 ml), cooled while being left standing, filtered and washed with toluene and a light yellow solid (2.4 g) was obtained.

1. temperatureunder refluxing for 10 hours
2. filtrationThe reaction mixture was filtered
3. washwashed with toluene, water and methanol
4. customa gray solid (1.4 g, the first crop, 25%) was obtained
5. customFrom the filtrate, the organic layer was separated
6. washwashed with a saturated aqueous solution of sodium chloride
7. dry with materialdried with magnesium sulfate
8. customThe solvent was removed by distillation
9. customa deep brown oil was obtained
10. customcrystals were formed soon
11. customThe formed crystals were separated by filtration
12. washwashed with a mixed solvent
13. customa white solid (3.3 g, the second crop, 59%) was obtained
14. customThe obtained crude crystals (3.5 g)
15. temperaturecooled
16. waitwhile being left standing
17. filtrationfiltered
18. washwashed with toluene