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Bromobenzene → 9,9''-Diphenyl-9H,9'H,9''H-3,3':6',3''-tercarbazole

HRID 1050709
Notes
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Reaction equation

HRID 1050709 reaction equation
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16](B4OC(C)(C)C(C)(C)O4)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:30]1[CH:31]=[CH:32][C:33]2[NH:34][C:35]3[C:40]([C:41]=2[CH:42]=1)=[CH:39][C:38](Br)=[CH:37][CH:36]=3.C([O-])([O-])=O.[K+].[K+].Br[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C1(C)C=CC=CC=1.O.CCO.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>[C:51]1([N:34]2[C:35]3[CH:36]=[CH:37][C:38]([C:11]4[CH:10]=[CH:9][C:8]5[NH:7][C:19]6[C:14]([C:13]=5[CH:12]=4)=[CH:15][C:16]([C:4]4[CH:3]=[CH:2][C:1]5[N:7]([C:19]7[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=7)[C:8]7[C:13]([C:6]=5[CH:5]=4)=[CH:12][CH:11]=[CH:10][CH:9]=7)=[CH:17][CH:18]=6)=[CH:39][C:40]=3[C:41]3[C:33]2=[CH:32][CH:31]=[CH:30][CH:42]=3)[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 2748743,6-DibromocarbazoleHCID 574156959-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole

Product 1

HCID 593067259,9''-Diphenyl-9H,9'H,9''H-3,3':6',3''-tercarbazoleYield 65.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole (7.1 g, 19.2 mmol), 3,6-dibromo-9H-carbazole (2.6 g, 8.0 mmol), K2CO3 (11.0 g, 79.7 mmol) in toluene (120 mL), water (40 mL) and EtOH (40 mL) was bubbled for 30 minutes with nitrogen. Then, Pd(PPh3)4 (0.9 g, 0.8 mmol) was added. The mixture was bubbled with nitrogen for 15 minutes and refluxed for 10 hours, after which bromobenzene (0.9 mL, 8.6 mmol) was added. The resultant mixture was refluxed for 6 hours. After cooling, the reaction mixture was extracted with CH2Cl2 and dried with MgSO4. The solvent was removed in vacuo and the residue was purified by flash chromatography using 40-60% CH2Cl2/hexane to afford 3,6-bis(9-phenylcarbazol-3-yl)carbazole (3.4 g, 65% yield) as a white solid.

Workup

  1. customThe mixture was bubbled with nitrogen for 15 minutes
  2. temperaturerefluxed for 10 hours
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted with CH2Cl2
  5. dry with materialdried with MgSO4
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7f3a8502306949178ead9adfc0d8248e
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09386657B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes