4-Bromodibenzothiophene → HCID 58479599, compound

HRID 1516998Notes

Reaction equation

HRID 1516998 reaction equation
Br[C:2]1[C:7]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][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:5]1[C:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[S:8][C:7]=2[C:2]([N:38]2[C:37]3[CH:36]=[CH:35][C:34]([C:30]4[CH:31]=[CH:32][C:33]5[N:21]([C:15]6[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=6)[C:22]6[C:27]([C:28]=5[CH:29]=4)=[CH:26][CH:25]=[CH:24][CH:23]=6)=[CH:46][C:45]=3[C:44]3[C:39]2=[CH:40][CH:41]=[CH:42][CH:43]=3)=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 4583524-BromodibenzothiopheneHCID 23676156Sodium t-butoxideHCID 593066299-Phenyl-9H,9'H-[3,3']bicarbazolyl

Product 1

HCID 58479599HCID 58479599, compoundYield 76%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 4-bromodibenzo[b,d]thiophene (2.061 g, 7.83 mmol), 9-phenyl-9H,9′H-3,3′-bicarbazole (2 g, 4.90 mmol), and sodium t-butoxide (1.412 g, 14.69 mmol) in 200 mL of xylene was bubbled with N2 for 20 min. Pd2(dba)3 (0.045 g, 0.049 mmol) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.080 g, 0.196 mmol) were added and bubbled with nitrogen for another 20 min, then the mixture was heated to reflux 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 2:3 dichloromethane and hexanes as solvent. 9-(dibenzo[b,d]thiophen-4-yl)-9′-phenyl-9H,9′H-3,3′-bicarbazole (2.2 g. 3.72 mmol, 76% yield) was obtained. The product was further purified by recrystallization with dichloromethane and hexane.

Workup

  1. customwas bubbled with N2 for 20 min
  2. custombubbled with nitrogen for another 20 min
  3. temperaturethe mixture was heated
  4. temperatureto reflux under N2 for 24 h
  5. temperatureThe mixture was cooled
  6. filtrationfiltered through Celite
  7. customAfter solvent evaporation
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-8e04e65685da42ab98a212a8c41ac2cc
Source dataset
uspto-grants-2012_07
Patent number
US08227801B2

Reaction notes

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