Ethyl Acetate → N-(4-cyano-2-fluoro-5-(trifluoromethyl)phenyl)acetamide
Reaktionsgleichung
Br[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([NH:12][C:13](=[O:15])[CH3:14])=[C:4]([F:16])[CH:3]=1.[C:17]([Cu])#[N:18].CCOC(C)=O>CN(C=O)C>[C:17]([C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([NH:12][C:13](=[O:15])[CH3:14])=[C:4]([F:16])[CH:3]=1)#[N:18]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
A mixture of compound 23 (300 mg, 1 mmol), CuCN (355 mg, 4 mmol) in DMF (6 mL) was heated at 150° C. under N2 overnight. The reaction mixture was cooled to room temperature and then poured into ice water. EtOAc was added and the insoluble solid was filtered off (rinsed with EtOAc). The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with aq.NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified with silica gel chromatography (PE:EtOAc=4:1) to afford the title compound 24 (140 mg, 28%) as a white solid. 1H NMR (400 MHz, CDCl3) δ8.99 (d, 1H, J=7.2 Hz), 7.55 (d, 1H, J=10.0 Hz), 2.92 (s, 3H).
Aufarbeitung
- temperatureThe reaction mixture was cooled to room temperature
- filtrationthe insoluble solid was filtered off
- wash(rinsed with EtOAc)
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with EtOAc
- washThe combined organic layers were washed with aq
- dry with materialNaHCO3 and brine, dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified with silica gel chromatography (PE:EtOAc=4:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-fde8eaaa87d243409581d7a5eada02e4
- Quelldatensatz
- uspto-grants-2015_12
- Patentnummer
- US09216957B2
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