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

HRID 2169686
Notes
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Reaction equation

HRID 2169686 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-691b965e48d94cde9bd66bf434a18661
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09048437B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes