Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Biphenyl-2-boronic acid | HCID 4589187 | — |
| Reactant | 2,8-Dibromo-6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene | HCID 58987286 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86722507 | HCID 86722507 | 57% |
Reaction Steps
A mixture of 14.7 g (31.5 mmol) of 2,8-dibromo-6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene, 6.5 g (33 mmol) of biphenyl-2-ylboronic acid, 0.36 g (0.3 mmol) of tetrakis(triphenylphosphine) palladium, 32 ml of 2M Na2CO3, 60 ml of EtOH and 150 ml toluene was degassed and placed under nitrogen, and then heated at 100° C. for 24 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica (hexane-dichloromethane) to give product 9.7 g (17.9 mmol, 57%). 1H NMR (CDCl3, 400 MHz): chemical shift (ppm): 7.78 (d, J=8.0 Hz, 1H), 7.65˜7.61 (m, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.51˜7.21 (m, 10H), 7.18 (s, 2H), 7.08˜6.99 (m, 2H), 1.83 (s, 6H), 1.81 (s, 6H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08993130B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-7d5685335743400b94e0afa49b1df72d |
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| Source note | uspto-grants-2015_03 |
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