Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | 2-Methylphenethyl alcohol | HCID 88267 | — |
| Edukt | 2-Formylphenylboronic acid | HCID 292189 | — |
| Edukt | 4-Bromo-3-fluorotoluene | HCID 573280 | — |
| Katalysator | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | 2-(2-Fluoro-4-methylphenyl)benzaldehyde | HCID 18357654 | 71,5% |
Reaktionsschritte
A mixture of 2 g of 4-bromo-3-fluorotoluene, 1.75 g of 2-formylbenzeneboronic acid, 0.36 g of tetrakis(triphenylphosphine)-palladium (0) and 11.6 ml of 2N aqueous sodium carbonate, in 50 ml of a 9:1 mixture of toluene-ethanol was heated to 100° C. for 3 h. The mixture was cooled to room temperature, diluted with 100 ml of methylene chloride and washed with 50 ml of 5% sodium bicarbonate containing 5 ml of 0.880 ammonia. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure. The resulting oil was purified by chromatography on silica gel eluting with ethyl acetate-heptane (1:3) to give 1.62 g of 2-(2-fluoro4-methylphenyl)benzaldehyde as an oil, GC-M.S. (E.I.) (M/Z): 214 [M+].
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US06313139B1 |
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| Quelldatensatz | uspto-grants-2001_11 |
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| ORD ID | ord-c66d846d101b483a9b567ded74e6d26c |
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| Quellennotiz | uspto-grants-2001_11 |
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