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

HRID 2169686
ノート
印刷プレビュー

反応式

HRID 2169686 の反応式
[CH3:1][C:2]1([CH3:36])[C:26]2[C:6]([CH:7]=[C:8]3[CH:25]=[C:24]4[C:11]([C:12]5[C:17]([C:18]6[C:23]4=[CH:22][CH:21]=[CH:20][CH:19]=6)=[CH:16][CH:15]=[CH:14][CH:13]=5)=[CH:10][C:9]3=2)=[CH:5][C:4](B2OC(C)(C)C(C)(C)O2)=[CH:3]1.Br[C:38]1[C:39]2[C:44]([C:45](C3C4C(=CC=CC=4)C(F)=CC=3)=[C:46]3[C:51]=1[CH:50]=[CH:49][CH:48]=[CH:47]3)=[CH:43][CH:42]=[CH:41][CH:40]=2.[C:63]([O-])([O-])=O.[Na+].[Na+].[CH2:69](O)[CH3:70].[C:72]1([CH3:78])[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1>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>[CH3:36][C:2]1([CH3:1])[C:26]2[C:6]([CH:7]=[C:8]3[CH:25]=[C:24]4[C:11]([C:12]5[C:17]([C:18]6[C:23]4=[CH:22][CH:21]=[CH:20][CH:19]=6)=[CH:16][CH:15]=[CH:14][CH:13]=5)=[CH:10][C:9]3=2)=[CH:5][C:4]([C:38]2[C:39]3[C:44]([C:45]([C:70]4[CH:69]=[CH:63][C:77]5[C:72](=[CH:73][CH:74]=[CH:75][CH:76]=5)[CH:78]=4)=[C:46]4[C:51]=2[CH:50]=[CH:49][CH:48]=[CH:47]4)=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:3]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 5

HCID 702EthanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 576946099-Bromo-10-(4-fluoronaphthalen-1-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 86718313
10,10-dimethyl-12-(10-(naphthalen-2-yl)anthracen-9-yl)-10H-indeno[1,2-b]triphenylene
収率 85%

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

実験手順

A three-necked 250 mL flask was charged with 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.0 g, 10.6 mmol), 9-bromo-10-(4-fluoronaphthalen-1-yl) anthracene (4.26 g, 10.6 mmol), Pd(PPh3)4 (0.25 g, 0.21 mmol), aqueous Na2CO3 (2.0 M, 12 mL, 23.4 mmol), ethanol (15 mL), and toluene (50 mL). The mixture was degassed and refluxed for 24 h under a nitrogen atmosphere. After being cooled, H2O (50 mL) was added to the mixture. The crude product was collected as a yellow-green solid powder by filtration and washed with methanol several times to remove impurity. It was dried at 20° C. under vacuum and gave a bright yellow-green solid product in 85% yield (6.01 g, 9.0 mmol). MS (m/z, FAB+): 664.8 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, 9H), 7.42˜7.28 (m, 4H), 7.20 (d, J=7.40 Hz, 1H), 1.76 (s, 6H).

後処理

  1. customThe mixture was degassed
  2. temperaturerefluxed for 24 h under a nitrogen atmosphere
  3. temperatureAfter being cooled
  4. additionH2O (50 mL) was added to the mixture
  5. filtrationThe crude product was collected as a yellow-green solid powder by filtration
  6. washwashed with methanol several times
  7. customto remove impurity
  8. customIt was dried at 20° C. under vacuum
  9. customgave a bright yellow-green solid product in 85% yield (6.01 g, 9.0 mmol)

出典と根拠

ORDレコード
ord-691b965e48d94cde9bd66bf434a18661
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09048437B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート