Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Bromopyrene | HCID 159627 | — |
| Reactant | 4-(1-Naphthyl)phenylboronic Acid (contains varying amounts of Anhydride) | HCID 44119399 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 86084118 | HCID 86084118 | 99.3% |
Reaction Steps
7.4 g of 4-(naphthalene-1-yl)phenyl boronic acid prepared by a well known method and 7.0 g of conventional 1-bromopyrene were dissolved in 80 ml of dimethoxyethane (DME). Subsequently, 0.58 g of tetrakistriphenylphosphine palladium and 40 ml of 2M-sodium carbonate aqueous solution were added therein, followed by argon displacement. After heating and refluxing over 8 hours, it was stood to cool and then an organic layer was extracted therefrom by toluene. The organic layer was washed by saturated salt water, followed by drying through anhydrous sodium sulfate, and then the organic solvent was removed by an evaporator. The residue was refined through a silica gel chromatography (a developing solvent: toluene) and then 10.0 g of 1-(4-naphthalene-1-yl-phenyl)pyrene was obtained. (yield: 99%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08318995B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-a82deb956ab14a7e930b1a817e77d010 |
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| Source note | uspto-grants-2012_11 |
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