Reaktionsgleichung
Br[C:2]1[C:11]([F:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([Cl:13])[CH:3]=1.[CH3:14][N:15](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Zn].C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[Cl:13][C:4]1[CH:3]=[C:2]([C:14]#[N:15])[C:11]([F:12])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 5
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
Methyl 4-bromo-2-chloro-5-fluorobenzoate (2.10 g; 7.85 mmol; 1 eq.), zinc cyanide (553.15 mg; 4.71 mmol), tris(dibenzylideneacetone)dipalladium(0) (57.52 mg; 0.06 mmol), 1,1′-bis(diphenylphosphino)ferrocene (69.64 mg; 0.13 mmol; 0.02 eq.), zinc (20.54 mg; 0.31 mmol; 0.04 eq.) and zinc acetate (57.62 mg; 0.31 mmol; 0.04 eq.) were put in dry DMF (21 mL). The reaction mixture was purged with N2 and then heated to 90° C. for 12 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with EtOAc. The organic phase was washed with water, brine, dried over MgSO4 and concentrated affording the title compound as a brown solid. It was purified by washing with EtOH affording the title compound as a beige solid used without further purification. 1H NMR (DMSO-d6, 300 MHz) δ 8.36-8.35 (m, 1H), 8-7.97 (m, 1H), 3.90 (s, 3H). HPLC (Method A) Rt 4.02 min (Purity: 92.5%).
Aufarbeitung
- customThe reaction mixture was purged with N2
- temperatureThe reaction mixture was cooled to RT
- filtrationfiltered over a pad of celite
- washwashed with EtOAc
- washThe organic phase was washed with water, brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-bbba3903b51d4da99a8510839015d8e4
- Quelldatensatz
- uspto-grants-2012_06
- Patentnummer
- US08202865B2
Verknüpfte Notizen
Wird geladen…