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

HRID 2280108ノート

反応式

HRID 2280108 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:40]2[N:39]([C:41]3[CH:46]=[CH:45][C:44]([C:47]4[CH:48]=[CH:49][C:50]5[NH:51][C:52]6[C:57]([C:58]=5[CH:59]=4)=[CH:56][CH:55]=[CH:54][CH:53]=6)=[CH:43][CH:42]=3)[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.CCCCCC>[CH:28]1[C:40]2[N:39]([C:41]3[CH:46]=[CH:45][C:44]([C:47]4[CH:48]=[CH:49][C:50]5[N:51]([C:2]6[CH:3]=[CH:4][C:5]([C:8]7[C:21]8[C:16]([C:15]([C:22]9[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=9)=[C:14]9[C:9]=7[CH:10]=[CH:11][CH:12]=[CH:13]9)=[CH:17][CH:18]=[CH:19][CH:20]=8)=[CH:6][CH:7]=6)[C:52]6[C:57]([C:58]=5[CH:59]=4)=[CH:56][CH:55]=[CH:54][CH:53]=6)=[CH:43][CH:42]=3)[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]=2[CH:31]=[CH:30][CH:29]=1

参加物

8

反応物 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 23676156Sodium t-butoxideHCID 593068843-(4-(9h-Carbazol-9-yl)phenyl)-9h-carbazole

生成物 1

HCID 593067693-[4-(9H-carbazol-9-yl)phenyl]-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole収率 81%

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2 回HCID 8058Hexane溶媒

実験手順

1.8 g (4.5 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 1.8 g (4.5 mmol) of 3-[4-(9H-carbazol-9-yl)phenyl]-9H-carbazole (CPC), and 1.1 g (10 mmol) of sodium tert-butoxide were put into a 200 mL three-neck flask. The air in the flask was replaced with nitrogen. To the mixture were added 25 mL of toluene and 0.10 mL of tri(tert-butyl)phosphine (a 10 wt % hexane solution). This mixture was stirred to be degassed while the pressure was reduced. After the degassing, 58 mg (0.10 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture. This mixture was refluxed and then cooled to room temperature. Then, to the mixture was added about 50 mL of toluene. The mixture was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was condensed to give a light yellow solid. This solid was recrystallized with toluene/hexane to give 2.6 g of a light yellow powdered solid, which was the object of the synthesis, at a yield of 81%. A synthesis scheme of Step 4 is shown in (f-4) given below.

後処理

  1. customto be degassed while the pressure
  2. temperatureThis mixture was refluxed
  3. filtrationThe mixture was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina
  4. customcondensed
  5. customto give a light yellow solid
  6. customThis solid was recrystallized with toluene/hexane

出典と根拠

ORDレコード
ord-57c42f5152e3443c94a9c2f94104a6ff
出典データセット
uspto-grants-2015_09
特許番号
US09136479B2

反応ノート

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