Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | 2-Bromo-4-methoxypyridine | HCID 4738484 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 18631004 | HCID 18631004 | 85.2% |
Reaction Steps
To a suspension of 2-bromo-4-methoxypyridine (0.94 g), 4-fluorophenylboronic acid (909 mg) and tetrakis(triphenylphosphine)-palladium (289 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (6.5 ml). The mixture was stirred at 80° C. for 4 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 50 g, 30% ethyl acetate in n-hexane) to give 4-(4-methoxypyridin-2-yl)fluorobenzene (0.866 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06521643B1 |
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| Source dataset | uspto-grants-2003_02 |
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| ORD ID | ord-2edcff9488b34b84b0e092023b733f56 |
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| Source note | uspto-grants-2003_02 |
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