Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | HCID 58894948 | HCID 58894948 | — |
| Reactant | 10,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 86718312 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86718315 | HCID 86718315 | 46.3% |
Reaction Steps
A mixture of 8.3 g (20.3 mmol) of 1-(6-bromonaphthalen-2-yl)pyrene, 9.5 g (20.3 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.29 g (0.25 mmol) of Tetrakis(triphenylphosphine)palladium, 17 ml of 2M Na2CO3, 40 ml of EtOH and 100 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 12 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 6.3 g (yield 46%) of yellow product which was recrystallized from toluene. MS(m/z,FAB+); 671.5; 1H NMR (CDCl3, 400 MHz): chemical shift(ppm) 9.01 (s, 1H), 8.52˜8.45 (m, 3H), 8.25 (s, 1H), 8.10˜7.89 (m, 9H), 7.78 (d, J=8.00 Hz, 1H), 7.66˜7.49 (m, 10H), 7.44 (d, J=8.00 Hz, 1H), 7.28 (d, J=8.00 Hz, 1H), 1.84 (s, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09260363B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-f7af2a4c4e5c4253a120310b7d747a4a |
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| Source note | uspto-grants-2016_02 |
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