Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | (2-Methylpropyl)boronic acid | HCID 2734395 | — |
| Edukt | 2-Bromo-5-nitrobenzonitrile | HCID 7095423 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Lösungsmittel | Diethyl Ether | HCID 3283 | — |
| Produkt | 2-Isobutyl-5-nitrobenzonitrile | HCID 22228030 | 58,9% |
Reaktionsschritte
Under an argon gas atmosphere, 2-bromo-5-nitrobenzonitrile (2.0 g), isobutylboronic acid (988 mg), cesium carbonate (5.7 g), and PdCl2 (dppf)-CH2Cl2 (720 mg) were dissolved in toluene (25 ml) and water (1 ml). The mixture was stirred at 100° C. for 18 hours. After the mixture was cooled to room temperature, the mixture was diluted with diethyl ether and water followed by the step of extraction/separation. The organic layer was washed with 1 N-hydrochloric acid, 5 N-sodium hydroxide aqueous solution and saturated brine, and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting residue was purified on column chromatography (EtOAc:hexane=1:3) to obtain the title compound (1.06 g) as a pale yellow oily substance.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08895753B2 |
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| Quelldatensatz | uspto-grants-2014_11 |
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| ORD ID | ord-2103f95a344443ddb9b588fb4cb385b3 |
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| Quellennotiz | uspto-grants-2014_11 |
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