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Carbazole → 9-[3-(10-phenyl-9-anthryl)phenyl]-9H-carbazole

HRID 1517157
Notes
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Reaction equation

HRID 1517157 reaction equation
Br[C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.[CH:28]1[C:40]2[NH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[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].C1(C)C=CC=CC=1>[C:14]1([C:15]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:8]([C:4]3[CH:3]=[C:2]([N:39]4[C:40]5[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=5[C:33]5[C:38]4=[CH:37][CH:36]=[CH:35][CH:34]=5)[CH:7]=[CH:6][CH:5]=3)=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[CH:20]3)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 593021329-(3-Bromophenyl)-10-phenylanthracene

Product 1

HCID 588760209-[3-(10-phenyl-9-anthryl)phenyl]-9H-carbazoleYield 73.4%

Reagents, catalysts & solvents 2

HCID 6505921
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
Catalyst
HCID 1140TolueneSolvent

Procedure

Into a 200 mL three-neck flask were put 1.3 g (3.3 mmol) of 9-(3-bromophenyl)-10-phenylanthracene (abbr: mPA), 0.55 g (3.3 mmol) of 9H-carbazole, and 0.63 g (6.6 mmol) of sodium tert-butoxide. After the air in the flask was replaced with nitrogen, 40 mL of toluene and 0.40 mL of tri(tert-butyl)phosphine (10 wt % hexane solution) were added to this mixture. This mixture was stirred to be degassed while the pressure was reduced. After the degassing, 95 mg (0.17 mmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture. This mixture was stirred under a nitrogen stream at 110° C. for 8 hours. After the stirring, this mixture was subjected to suction filtration through Celite (Wako Pure Chemical Industries, Ltd., catalog No.: 531-16855), alumina, and Florisil (Wako Pure Chemical Industries, Ltd., catalog No.: 540-00135). The obtained filtrate was concentrated to give a light-yellow oily substance. The obtained oily substance was recrystallized from toluene/hexane to give 1.2 g of a light-yellow solid, which was the object of the synthesis, in a yield of 71%.

Workup

  1. customInto a 200 mL three-neck flask were put
  2. additionwere added to this mixture
  3. customto be degassed while the pressure
  4. stirringThis mixture was stirred under a nitrogen stream at 110° C. for 8 hours
  5. filtrationAfter the stirring, this mixture was subjected to suction filtration through Celite (Wako Pure Chemical Industries, Ltd., catalog No.: 531-16855), alumina, and Florisil (Wako Pure Chemical Industries, Ltd., catalog No.: 540-00135)
  6. concentrationThe obtained filtrate was concentrated
  7. customto give a light-yellow oily substance
  8. customThe obtained oily substance was recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-cb592d3f43504ec794104061a5cb8696
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08231942B2

Reaction notes

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