Reaktion #988944

Reaktionsgleichung

9-bromo-10-(4-bromophenyl)-anthracene

sodium carbonate

toluene

toluene

4-(2,2-diphenylvinyl)phenylboronic acid

→

solid

9-(3-(2,2-diphenylvinyl)phenyl)-10-(4-(3-(2,2-diphenyl-vinyl)phenyl)phenyl)anthracene

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder refluxing for 10 hours
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Waschenwashed with toluene, water and methanol
4. 4
   Sonstigea gray solid (1.4 g, the first crop, 25%) was obtained
5. 5
   SonstigeFrom the filtrate, the organic layer was separated
6. 6
   Waschenwashed with a saturated aqueous solution of sodium chloride
7. 7
   Trocknendried with magnesium sulfate
8. 8
   SonstigeThe solvent was removed by distillation
9. 9
   Sonstigea deep brown oil was obtained
10. 10
    Sonstigecrystals were formed soon
11. 11
    SonstigeThe formed crystals were separated by filtration
12. 12
    Waschenwashed with a mixed solvent
13. 13
    Sonstigea white solid (3.3 g, the second crop, 59%) was obtained
14. 14
    SonstigeThe obtained crude crystals (3.5 g)
15. 15
    Temperaturcooled
16. 16
    workup.WAITwhile being left standing
17. 17
    Filtrationfiltered
18. 18
    Waschenwashed with toluene

Vorschrift

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.

Quelle