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

HRID 1827625Notes

Reaction equation

HRID 1827625 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+]>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.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 178418397HCID 178418397, compoundCatalystHCID 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-cbfac56abcf64b8f8aa82082e0919917
Source dataset
uspto-grants-2006_05
Patent number
US07053255B2

Reaction notes

Loading…