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

HRID 1747206
ノート
印刷プレビュー

反応式

HRID 1747206 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒
HCID 1140Toluene溶媒
HCID 8058Hexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b15e93f4dda84e0ebbc876958a79b2e7
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150551B2

反応ノート

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