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Tris(1,1-dimethylethyl)phosphine → 3-(Dibenzofuran-2-yl)-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole

HRID 1747206
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HRID 1747206 반응식
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:36]2[C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[O:33][C:32]=2[CH:31]=[CH:30][C:29]=1[C:41]1[CH:42]=[CH:43][C:44]2[NH:45][C:46]3[C:51]([C:52]=2[CH:53]=1)=[CH:50][CH:49]=[CH:48][CH:47]=3.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>[CH:28]1[C:36]2[C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[O:33][C:32]=2[CH:31]=[CH:30][C:29]=1[C:41]1[CH:42]=[CH:43][C:44]2[N:45]([C:2]3[CH:3]=[CH:4][C:5]([C:8]4[C:21]5[C:16]([C:15]([C:22]6[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=6)=[C:14]6[C:9]=4[CH:10]=[CH:11][CH:12]=[CH:13]6)=[CH:17][CH:18]=[CH:19][CH:20]=5)=[CH:6][CH:7]=3)[C:46]3[C:51]([C:52]=2[CH:53]=1)=[CH:50][CH:49]=[CH:48][CH:47]=3
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 23676156Sodium t-butoxideHCID 579976693-(Dibenzofuran-2-yl)-9H-carbazole

생성물 1

HCID 866645023-(Dibenzofuran-2-yl)-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole수율 81.4%

시약·촉매·용매 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매
HCID 1140Toluene용매
HCID 8058Hexane용매

실험 절차

Into a 200-mL three-neck flask were put 1.0 g (2.6 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 0.86 g (2.6 mmol) of 3-(dibenzofuran-2-yl)-9H-carbazole, and 0.50 g (5.2 mmol) of sodium tert-butoxide. The air in the flask was replaced with nitrogen, and then, to the mixture were added 50 mL of toluene and 0.20 mL of tri(tert-butyl)phosphine (a 10 wt % hexane solution). This mixture was degassed under reduced pressure while being stirred, and then 75 mg (0.13 mmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture. This mixture was stirred at 110° C. for 2 hours under a nitrogen stream. After the stirring, this mixture was subjected to suction filtration through Celite, alumina, and Florisil. The obtained filtrate was concentrated to give a light-yellow oily substance. This oily substance was recrystallized from toluene/hexane to give 1.4 g of light-yellow powder in 80% yield. The synthesis scheme of Step 4 is shown in (a-4).

후처리

  1. customInto a 200-mL three-neck flask were put
  2. customThis mixture was degassed under reduced pressure
  3. stirringThis mixture was stirred at 110° C. for 2 hours under a nitrogen stream
  4. filtrationAfter the stirring, this mixture was subjected to suction filtration through Celite, alumina, and Florisil
  5. concentrationThe obtained filtrate was concentrated
  6. customto give a light-yellow oily substance
  7. customThis oily substance was recrystallized from toluene/hexane

출처 및 근거

ORD 기록
ord-b15e93f4dda84e0ebbc876958a79b2e7
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150551B2

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