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

HRID 578605
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HRID 578605 반응식
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
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 1140Toluene용매

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온도
90 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-677457d037fe4ad89952f5b097f878ee
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040174B2

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