HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1,2-Dimethoxyethane → 5-(2-Fluoro-3-methoxyphenyl)-2-methylfuran-3-carbaldehyde
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 1,2-Dimethoxyethane | HCID 8071 | — |
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | 2-Fluoro-3-methoxyphenylboronic acid | HCID 4985744 | — |
| Edukt | 5-Bromo-2-methylfuran-3-carbaldehyde | HCID 46941673 | — |
| Katalysator | HCID 178418397 | HCID 178418397 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Produkt | 5-(2-Fluoro-3-methoxyphenyl)-2-methylfuran-3-carbaldehyde | HCID 86646381 | 93,1% |
Reaktionsschritte
A mixture of 5-bromo-2-methylfuran-3-carbaldehyde (1.3 g), 2-fluoro-3-methoxyphenylboronic acid (1.4 g), tetrakis(triphenylphosphine)palladium(0) (0.4 g), 2N aqueous sodium carbonate solution (9 mL) and 1,2-dimethoxyethane (20 mL) was stirred overnight with refluxing under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 30% ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (1.5 g, 93%) as a yellow crystal.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08309580B2 |
| Quelldatensatz | uspto-grants-2012_11 |
| ORD ID | ord-16c23b011cfe4399839ec491acacc64a |
| Quellennotiz | uspto-grants-2012_11 |