Hydrochloric Acid → HCID 66642757, Verbindung
Reaktionsgleichung
C([O:9][C:10]1[CH:15]=[C:14](I)[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH:26]([CH3:28])[CH3:27])[CH:19]=2)=[C:12](I)[CH:11]=1)(=O)C1C=CC=CC=1.[C:30]([Cu])#[N:31].Cl.[CH3:34][N:35](C=O)C>>[C:34]([C:14]1[CH:15]=[C:10]([OH:9])[CH:11]=[C:12]([C:30]#[N:31])[C:13]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH:26]([CH3:27])[CH3:28])[CH:19]=1)#[N:35]Komponenten
Reaktionsbedingungen
- Temperatur
- 160 °C
Versuchsvorschrift
To a stirred solution of 3,5-diiodo-4-(4′-methoxy-3′-iso-propylphenoxy)phenyl benzoate (0.4 g, 0.76 mmol) in DMF(5.0 mL) at rt was added CuCN (0.27 g, 3.0 mmol). The reaction mixture was heated at 160° C. for 5 min under microwave irradiation, the reaction mixture was cool to room temperature and poured into 1N HCl (50 mL) and extracted with ethyl acetate (100 mL×2). The organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (3:7) to afford 3,5-dicyano-4-(4′-methoxy-3′-iso-propylphenoxy)phenol as a viscous oil (105 mg, 35%): 1H NMR (300 MHz, CDCl3): δ 7.35 (s, 2 H), 6.99 (d, J=3.0 Hz, 1 H), 6.78 (d, J=8.7 Hz, 1 H), 6.99 (dd, J=3.0, 8.7 Hz, 1 H), 3.84 (s, 3 H), 3.38-3.30 (m, 1 H), 1.21 (d, J=6.9 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-ethyl acetate (7:3); Rf=0.38.
Aufarbeitung
- temperaturethe reaction mixture was cool to room temperature
- extractionextracted with ethyl acetate (100 mL×2)
- dry with materialThe organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel
- washeluting with ethyl acetate-hexanes (3:7)
Quellen und Nachweise
- ORD-Eintrag
- ord-e8d1bb447eaf4a12b414c49963fe25a6
- Quelldatensatz
- uspto-grants-2009_04
- Patentnummer
- US07514419B2
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