Ethanol → 10,10-dimethyl-12-(10-(naphthalen-2-yl)anthracen-9-yl)-10H-indeno[1,2-b]triphenylene

HRID 1775392

反応式

HRID 1775392 の反応式
Br[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH3:26][C:27]1([CH3:61])[C:51]2[C:31]([CH:32]=[C:33]3[CH:50]=[C:49]4[C:36]([C:37]5[C:42]([C:43]6[C:48]4=[CH:47][CH:46]=[CH:45][CH:44]=6)=[CH:41][CH:40]=[CH:39][CH:38]=5)=[CH:35][C:34]3=2)=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28]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.C1(C)C=CC=CC=1>[CH3:61][C:27]1([CH3:26])[C:51]2[C:31]([CH:32]=[C:33]3[CH:50]=[C:49]4[C:36]([C:37]5[C:42]([C:43]6[C:48]4=[CH:47][CH:46]=[CH:45][CH:44]=6)=[CH:41][CH:40]=[CH:39][CH:38]=5)=[CH:35][C:34]3=2)=[CH:30][C:29]([C:2]2[C:3]3[C:8]([C:9]([C:16]4[CH:25]=[CH:24][C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[CH:17]=4)=[C:10]4[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:28]1

参加物

7

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 161162639-Bromo-10-(naphthalen-2-yl)anthraceneHCID 8671831210,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 8671831310,10-dimethyl-12-(10-(naphthalen-2-yl)anthracen-9-yl)-10H-indeno[1,2-b]triphenylene収率 53%

試薬・触媒・溶媒 2

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

反応条件

温度
90 °C

実験手順

A mixture of 6.6 g (17.2 mmol) of 9-bromo-10-(naphthalene-2-yl)anthracene, 8.1 g (17.2 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.2 g (0.172 mmol) of Tetrakis(triphenylphosphine)palladium, 13 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 the reaction finish, the mixture was allowed to cool to room temperature. Than 500 ml MeOH was added, while stirring and the precipitated product was filtered off with suction. To give 5.9 g (yield 53%) of yellow product which was recrystallized from toluene. MS(m/z,FAB+): 646.4; 1H NMR (CDCl3, 400 MHz): chemical shift(ppm) 9.14 (s, 1H), 8.90 (d, J=7.80 Hz, 1H), 8.82 (d, J=7.92 Hz, 1H), 8.79 (s, 1H), 8.73 (d, J=7.88 Hz, 2H), 8.23 (d, J=7.72 Hz, 1H), 8.11 (d, J=8.24 Hz, 1H), 8.07˜8.02 (m, 2H), 7.96 (d, J=7.40 Hz, 1H), 7.89 (d, J=8.64 Hz, 2H), 7.78˜7.59 (m, 10H), 7.42˜7.33 (m, 4H), 7.20 (d, J=7.40 Hz, 1H), 1.76 (s, 6H).

後処理

  1. customwas degassed
  2. temperatureto cool to room temperature
  3. additionThan 500 ml MeOH was added
  4. filtrationthe precipitated product was filtered off with suction

出典と根拠

ORDレコード
ord-0235cc6c3ca042f9894b2e2b788cf6ec
出典データセット
uspto-grants-2016_02
特許番号
US09260363B2

関連ノート

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