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

HRID 80291
ノート
印刷プレビュー

反応式

HRID 80291 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

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

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-6c133d6636e04d569177af9674ba1131
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08845926B2

反応ノート

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