Ethanol → 4-(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-phenylamine
Reaktionsgleichung
C(O)C.[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=3)[C:12]=2[F:29])[CH:8]=[CH:9][CH:10]=1>[Fe].O>[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([NH2:26])=[CH:24][CH:25]=3)[C:12]=2[F:29])[CH:8]=[CH:9][CH:10]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 85 °C
Versuchsvorschrift
In an 18 mL vial equipped with a stir bar was placed iron powder (179 mg, 3.20 mmol), ethanol (5.0 mL) and water (1.2 mL). The mixture was heated to 85° C. in an oil bath and then the above product 3′-Chloro-2-fluoro-6-methoxy-3-(4-nitro-benzyl)-biphenyl (6) (340 mg, 0.914 mmol) was added and the reaction was continued at 85° C. for 2 hours. The reaction mixture was cooled to room temperature and filtered through Celite. To the filtrate was added water (50 mL) and extractions were performed with ethyl acetate (2×60 mL). The organic portions were combined, washed with brine (50 mL), dried (MgSO4) and concentrated to produce 245 mg of 4-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-phenylamine (I-35) as a yellow, viscous oil in 79% yield. MS (APCI+): 342.0 (M+1).
Aufarbeitung
- customIn an 18 mL vial equipped with a stir bar
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered through Celite
- additionTo the filtrate was added
- extractionwater (50 mL) and extractions
- washwashed with brine (50 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-8dbc857c3542494696f8b7de4e912620
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08791267B2
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