2-Bromodibenzothiophene → HCID 58479588、化合物

HRID 1516997

反応式

HRID 1516997 の反応式
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

参加物

7

反応物 3

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

生成物 1

HCID 58479588HCID 58479588、化合物収率 58.1%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl触媒HCID 7237O-Xylene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-525eec47f4af44c2a6e48cc9f161a764
出典データセット
uspto-grants-2012_07
特許番号
US08227801B2

関連ノート

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