1,3-Dibromopropane → 3-Bromopropyl 2-chloro-4-(2,2,2-trifluoroethoxy)phenyl ether
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:4][C:3]=1[OH:14].[Br:15][CH2:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([F:12])([F:13])[F:11])[CH:5]=[CH:4][C:3]=1[O:14][CH2:18][CH2:17][CH2:16][Br:15]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
To a 110 ml DMF solution of 2-chloro-4-(2,2,2-trifluoroethoxy)phenol (5 g, 22.1 mmol) was added 1,3-dibromopropane (11.2 ml, 110 mmol) and cesium carbonate (9.34 g, 28.7 mmol). The resulting suspension was heated to 70° C. for 5 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel eluting with 10% dichloromethane/hexanes to give the title compound as a clear oil 4.37 g (57%).
Aufarbeitung
- customThe solvent was removed under reduced pressure
- additionThe residue was diluted with AcOEt and 2N hydrochloric acid
- customThe organic layer was separated
- extractionthe aqueous layer was extracted twice with AcOEt
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customchromatographed on silica gel eluting with 10% dichloromethane/hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-ecdd914637784e7789d3e00ed980906a
- Quelldatensatz
- uspto-grants-2004_03
- Patentnummer
- US06713508B2
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