Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | 2-Bromo-5-hydroxybenzaldehyde | HCID 387179 | — |
| Edukt | (R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane | HCID 2734443 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | HCID 86653794 | HCID 86653794 | 56% |
Reaktionsschritte
To a solution of 2-bromo-5-hydroxybenzaldehyde (62; 5 g, 0.025 mol) in DMF (100 ml) was added (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (63; 4.87 g, 0.032 mol) and K2CO3 (7.0 g, 0.05 mol). The resulting reaction mixture was stirred at 150° C. for 10 h, cooled to room temperature, diluted with water, and then extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether/EtOAc=10:1 to afford the desired product, namely (S)-2-bromo-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzaldehyde 64 (4.1 g, 56%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08846947B2 |
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| Quelldatensatz | uspto-grants-2014_09 |
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| ORD ID | ord-7cb895ee291041ef807b9d856cc72837 |
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| Quellennotiz | uspto-grants-2014_09 |
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