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Ethanol → 10,10,10',10'-tetramethyl-10H,10'H-12,12'-biindeno[1,2-b]triphenylene

HRID 578605
ノート
印刷プレビュー

反応式

HRID 578605 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:24]([C:25]([CH3:28])([CH3:27])[CH:26]=1)=[C:7]1[CH:8]=[C:9]3[C:22](=[CH:23][C:6]1=[CH:5]2)[C:21]1[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:15]1[C:10]3=[CH:11][CH:12]=[CH:13][CH:14]=1.[CH3:29][C:30]1([CH3:64])[C:54]2[C:34]([CH:35]=[C:36]3[CH:53]=[C:52]4[C:39]([C:40]5[C:45]([C:46]6[C:51]4=[CH:50][CH:49]=[CH:48][CH:47]=6)=[CH:44][CH:43]=[CH:42][CH:41]=5)=[CH:38][C:37]3=2)=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31]1.C([O-])([O-])=O.[Na+].[Na+].CCO>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO.C1(C)C=CC=CC=1>[CH3:27][C:25]1([CH3:28])[C:24]2[C:4]([CH:5]=[C:6]3[CH:23]=[C:22]4[C:9]([C:10]5[C:15]([C:16]6[C:21]4=[CH:20][CH:19]=[CH:18][CH:17]=6)=[CH:14][CH:13]=[CH:12][CH:11]=5)=[CH:8][C:7]3=2)=[CH:3][C:2]([C:32]2[CH:33]=[C:34]3[C:54]([C:30]([CH3:64])([CH3:29])[CH:31]=2)=[C:37]2[CH:38]=[C:39]4[C:52](=[CH:53][C:36]2=[CH:35]3)[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:45]2[C:40]4=[CH:41][CH:42]=[CH:43][CH:44]=2)=[CH:26]1
参加物反応条件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 702EthanolHCID 10340Sodium CarbonateHCID 8671831210,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 8672032712-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene

生成物 1

HCID 8672032610,10,10',10'-tetramethyl-10H,10'H-12,12'-biindeno[1,2-b]triphenylene収率 49%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

A mixture of 4.2 g (10 mmol) of 12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene, 5.2 g (11 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.12 g (0.1 mmol) of Tetrakis(triphenylphosphine)Palladium, 15 ml of 2M Na2CO3, 30 ml of EtOH and 100 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 24 h. After finishing the reaction, The mixture was allowed to cool to room temperature. Than 100 ml MeOH was added, while stirring and the precipitated product was filtered off with suction. To give 3.3 g (yield 49%) of yellow product which was recrystallized from chloroform. MS (m/z, EI): 686.7. 1H NMR (CDCl3, 400 MHz): δ 9.05 (s, 2H), 8.86 (d, J=7.88 Hz, 2H), 8.79 (d, J=7.76 Hz, 2H), 8.74 (s, 2H), 8.71 (d, J=7.84 Hz, 4H), 8.10 (d, J=7.64 Hz, 2H), 7.84 (s, 2H), 7.81 (d, J=7.80 Hz, 2H), 7.76˜7.67 (m, 8H), 1.77 (s, 12H).

後処理

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. filtrationthe precipitated product was filtered off with suction

出典と根拠

ORDレコード
ord-677457d037fe4ad89952f5b097f878ee
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040174B2

反応ノート

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