Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Naphthaleneboronic acid | HCID 254532 | — |
| Reactant | 3,6-Dibromocarbazole | HCID 274874 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 85975625 | HCID 85975625 | 89% |
Reaction Steps
Firstly, 8.12 g (25.0 mmol) of 3,6-dibromo-carbazole and 9.46 g (55.0 mmol) of 1-Naphthylboronic acid are dissolved in 100 ml of toluene, and then an aqueous solution of 30 ml of 2M sodium carbonate (Na2CO3) and 30.0 ml of ethanol is added to the above-mentioned solution. After the mixed solution is degassed with nitrogen for 30 minutes, 577 mg (0.5 mmol) of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) is added to the solution under nitrogen and then the solution is heated to 90° C. After reacting for 8 hours, the solution is cooled to room temperature, added and stirred with methylene chloride and deionized water. Then, the extracted organic layer is dried with anhydrous magnesium sulfate (MgSO4), and the solvent is removed by reducing the pressure. The remains are passed through the silica gel column with petroleum ether:methylene chloride (V:V)=2:1 to obtain a white solid of 9.3 g (22.2 mmol, 89% yield) of 3,6-bis(1-naphthyl) carbazole. The specific reaction is shown in the reaction formula (1-A):
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09059413B1 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-3d4042d96a1e4b19bb7ba8fe7e404935 |
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| Source note | uspto-grants-2015_06 |
|---|