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

HRID 2169686
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HRID 2169686 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 1

HCID 86718313
10,10-dimethyl-12-(10-(naphthalen-2-yl)anthracen-9-yl)-10H-indeno[1,2-b]triphenylene
수율 85%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-691b965e48d94cde9bd66bf434a18661
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09048437B2

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