Water → 3-Bromo-5-chlorophenyl 2-chloro-5-fluorophenyl ether
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[Br:10][C:11]1[CH:16]=[C:15](F)[CH:14]=[C:13]([Cl:18])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][C:15]1[CH:14]=[C:13]([Cl:18])[CH:12]=[C:11]([Br:10])[CH:16]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 140 °C
Versuchsvorschrift
To a solution of 2-chloro-5-fluorophenol (82.3 g, 562 mmol) and 1-bromo-3-chloro-5-fluorobenzene (124 g, 590 mmol) in NMP (200 mL) was added potassium carbonate (155 g, 1.123 mol). The resulting mixture was then heated to 140° C. and maintained at 140° C. for hours, after which the mixture was poured into water (1500 mL) and extracted with EtOAc (2500+1500 mL). The combined extracts were washed with water and brine. This solution was concentrated on the rotary evaporator and the residue was distilled at high vacuum at 135-190° C. to give the title compound as a clear, colorless liquid. 1H NMR (CDCl3) δ 7.45 (dd, 1H, J=9.0 and 4.5 hz), 7.28 (dd, 1H, J=1.7 Hz), 7.26 (s, 1H), 7.00 (dd, 1 h, J=1.95 Hz), 6.92 (ddd, 1H, J=10.5, 7.6 and 2.7 Hz), 6.89 (dd, 1H, J=1.95 Hz).
Aufarbeitung
- temperaturemaintained at 140° C. for hours
- extractionextracted with EtOAc (2500+1500 mL)
- washThe combined extracts were washed with water and brine
- concentrationThis solution was concentrated on the rotary evaporator
- distillationthe residue was distilled at high vacuum at 135-190° C.
Quellen und Nachweise
- ORD-Eintrag
- ord-de67f5cab821498dbf33469186e5a095
- Quelldatensatz
- uspto-grants-2010_08
- Patentnummer
- US07781454B2
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