7H-Dibenzo(c,g)carbazole → 7-[4-(10-Phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole

HRID 876187Notes

Reaction equation

HRID 876187 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:14]([C:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:16]4[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]4)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.[CH:28]1[C:44]2[C:43]3[C:42]4[C:41]5[CH:45]=[CH:46][CH:47]=[CH:48][C:40]=5[CH:39]=[CH:38][C:37]=4[NH:36][C:35]=3[CH:34]=[CH:33][C:32]=2[CH:31]=[CH:30][CH:29]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>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].CCCCCC.C1(C)C=CC=CC=1>[C:14]1([C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8]([C:5]3[CH:4]=[CH:3][C:2]([N:36]4[C:37]5[CH:38]=[CH:39][C:40]6[CH:48]=[CH:47][CH:46]=[CH:45][C:41]=6[C:42]=5[C:43]5[C:44]6[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=6[CH:33]=[CH:34][C:35]4=5)=[CH:7][CH:6]=3)=[C:27]3[C:22]=2[CH:23]=[CH:24][CH:25]=[CH:26]3)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 91347H-Dibenzo(c,g)carbazoleHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 23676156Sodium t-butoxide

Product 1

HCID 866758387-[4-(10-Phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazoleYield 70%

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

In a 100 mL three-neck flask were placed 2.3 g (5.6 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 1.5 g (5.6 mol) of 7H-dibenzo[c,g]carbazole, and 1.2 g (12 mmol) of sodium tert-butoxide. After the air in the flask was replaced with nitrogen, to this mixture were added 30 mL of toluene and 2.8 mL of tri-(tert-butyl)phosphine (a 10 wt % hexane solution). This mixture was degassed by being stirred while the pressure was reduced. After the degassing, 0.16 g (0.28 mmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture. This mixture was stirred at 110° C. for 17 hours under a nitrogen stream, so that a solid was precipitated. The precipitated solid was removed by suction filtration. The collected solid was dissolved in about 30 mL of hot toluene, and this solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). A solid obtained by concentration of the filtrate was recrystallized from toluene/hexane to give 2.3 g of a pale yellow powder, which was the object of the synthesis, in a yield of 70%. A reaction scheme (c-1) of Step 3 is illustrated below.

Workup

  1. customIn a 100 mL three-neck flask were placed
  2. customThis mixture was degassed
  3. stirringThis mixture was stirred at 110° C. for 17 hours under a nitrogen stream
  4. customso that a solid was precipitated
  5. customThe precipitated solid was removed by suction filtration
  6. dissolutionThe collected solid was dissolved in about 30 mL of hot toluene
  7. filtrationthis solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135)
  8. customA solid obtained by concentration of the filtrate
  9. customwas recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-f342edf0190245bab1167bd0a9ac0660
Source dataset
uspto-grants-2015_03
Patent number
US08986857B2

Reaction notes

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