Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1,4-Dibromonaphthalene | HCID 66521 | — |
| Reactant | (Naphthalen-2-yl)boronic acid | HCID 2734375 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 23110736 | HCID 23110736 | 25.3% |
Reaction Steps
Under an argon gas atmosphere, 121 g (700 mmol) of 2-naphthaleneboronic acid, 200.0 g (700 mmol) of 1,4-dibromonaphthalene, 16.2 g (13.4 mmol) of tetrakis(triphenylphosphine) palladium(0), 3.0L of toluene, 3.2L of dimethoxyethane and 1.60L of 2M sodium carbonate solution were mixed, and stirred for 20 hours at 78 degrees C. The reaction mixture experienced filtration to be subsequently cleansed by water and methanol. The obtained solid was added with toluene to be heat-dissolved. Insoluble matter therein was eliminated by filtration, such that the filtrate was distilled away under reduced pressure. By recrystallizing residue by toluene and hexane, 59 g of 4-bromo-1-(2-naphthyl)naphthalene was obtained at an yield of 25%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08034256B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-5ff77ae854f54163988156824c1b5af5 |
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| Source note | uspto-grants-2011_10 |
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