Toluene → 9-(3-(2,2-Diphenylvinyl)phenyl)-10-(4-(3-(2,2-diphenyl-vinyl)phenyl)phenyl)anthracene

HRID 901762Notes

Reaction equation

HRID 901762 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:23]1([C:29]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:30][C:31]2[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:46]1([CH3:52])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:23]1([C:29]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:30][C:31]2[CH:36]=[C:35]([C:2]3[C:3]4[C:8]([C:9]([C:16]5[CH:21]=[CH:20][C:19]([C:48]6[CH:49]=[CH:50][CH:51]=[C:46]([CH:52]=[C:2]([C:3]7[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=7)[C:15]7[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=7)[CH:47]=6)=[CH:18][CH:17]=5)=[C:10]5[C:15]=3[CH:14]=[CH:13][CH:12]=[CH:11]5)=[CH:7][CH:6]=[CH:5][CH:4]=4)[CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 1140Toluene2×HCID 10340Sodium CarbonateHCID 11392411(4-(2,2-Diphenylvinyl)phenyl)boronic acidHCID 221380389-Bromo-10-(4-bromophenyl)anthracene

Product 1

HCID 178563809-(3-(2,2-Diphenylvinyl)phenyl)-10-(4-(3-(2,2-diphenyl-vinyl)phenyl)phenyl)anthracene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5d4c5d8a3dfe4676990b59afd47c94d1
Source dataset
uspto-grants-2008_04
Patent number
US07361796B2

Reaction notes

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