2-Bromodibenzothiophene → 9-(dibenzo[b,d]thiophen-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole

HRID 1516997Notes

Reaction equation

HRID 1516997 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[C:15]1([N:21]2[C:33]3[CH:32]=[CH:31][C:30]([C:34]4[CH:35]=[CH:36][C:37]5[NH:38][C:39]6[C:44]([C:45]=5[CH:46]=4)=[CH:43][CH:42]=[CH:41][CH:40]=6)=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC(C)([O-])C.[Na+]>C1(C)C(C)=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH:3]1[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[S:6][C:5]=2[CH:13]=[CH:14][C:2]=1[N:38]1[C:37]2[CH:36]=[CH:35][C:34]([C:30]3[CH:31]=[CH:32][C:33]4[N:21]([C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)[C:22]5[C:27]([C:28]=4[CH:29]=3)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:46][C:45]=2[C:44]2[C:39]1=[CH:40][CH:41]=[CH:42][CH:43]=2

Participants

7

Reactant 3

HCID 2995082-BromodibenzothiopheneHCID 23676156Sodium t-butoxideHCID 593066299-Phenyl-9H,9'H-[3,3']bicarbazolyl

Product 1

HCID 584795889-(dibenzo[b,d]thiophen-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazoleYield 58.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 2-bromodibenzo[b,d]thiophene (3.22 g, 12.24 mmol), 9-phenyl-9H-9′H-3,3′-bicarbazole (2.5 g, 6.12 mmol), and sodium t-butoxide (1.764 g, 18.36 mmol) in 100 mL of xylene was bubbled with N2 for 20 min. Pd2(dba)3 (0.056 g, 0.061 mmol) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.100 g, 0.245 mmol) were then added, and mixture was then bubbled with nitrogen for another 20 min. The reaction mixture was refluxed under N2 for 24 h. The mixture was cooled and filtered through Celite. After solvent evaporation, the residue was coated on Celite and purified by column chromatography using up to 50% dichloromethane in hexane as solvent. 9-(dibenzo[b,d]thiophen-2-yl)-9′-phenyl-9H,9′H-3,3′-bicarbazole (2.1 g, 3.55 mmol, 58.1% yield) was obtained.

Workup

  1. customwas bubbled with N2 for 20 min
  2. custommixture was then bubbled with nitrogen for another 20 min
  3. temperatureThe reaction mixture was refluxed under N2 for 24 h
  4. temperatureThe mixture was cooled
  5. filtrationfiltered through Celite
  6. customAfter solvent evaporation
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-525eec47f4af44c2a6e48cc9f161a764
Source dataset
uspto-grants-2012_07
Patent number
US08227801B2

Reaction notes

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