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

HRID 80291
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HRID 80291 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-6c133d6636e04d569177af9674ba1131
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08845926B2

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