Sodium Carbonate → 9-(4-(2,2-Diphenylvinyl)phenyl)-10-(4-(2-phenylvinyl)phenyl)anthracene

HRID 901766Notes

Reaction equation

HRID 901766 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[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:30]1([C:36]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:37][C:38]2[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:30]1([C:36]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:37][C:38]2[CH:43]=[CH:42][C:41]([C:2]3[C:3]4[C:8]([C:9]([C:16]5[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]6[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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:40][CH:39]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11392411(4-(2,2-Diphenylvinyl)phenyl)boronic acidHCID 738668529-Bromo-10-(4-(2-phenylvinyl)phenyl)anthracene

Product 1

HCID 738668539-(4-(2,2-Diphenylvinyl)phenyl)-10-(4-(2-phenylvinyl)phenyl)anthraceneYield 88%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent2×

Procedure

Under an atmosphere of argon, 9-bromo-10-(4-(2-phenylvinyl)-phenyl)anthracene (3.1 g, 7.1 mmole), 4-(2,2-diphenylvinyl)phenylboronic acid (2.4 g, 8.0 mmole, 1.1 eq) and tetrakis(triphenylphosphine)-palladium(0) (0.16 g, 0.14 mmole, 2% Pd) were suspended into toluene (25 ml). To the obtained suspension, a 2 M aqueous solution of sodium carbonate (2.5 g, 24 mmole, 3 eq/12 ml) was added and the resultant mixture was heated under refluxing for 10 hours. The reaction mixture was filtered and washed with water and methanol and a yellow solid was obtained. The obtained solid was suspended in boiling toluene (50 ml), cooled while being left standing, filtered and washed with toluene and a light yellow solid (3.8 g, 88%) was obtained.

Workup

  1. temperatureunder refluxing for 10 hours
  2. filtrationThe reaction mixture was filtered
  3. washwashed with water and methanol
  4. customa yellow solid was obtained
  5. temperaturecooled
  6. waitwhile being left standing
  7. filtrationfiltered
  8. washwashed with toluene

Sources & evidence

ORD record
ord-d3ed411092ed473a9b0023ebd237e5f9
Source dataset
uspto-grants-2008_04
Patent number
US07361796B2

Reaction notes

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