Reaktionsgleichung
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH2:19]([O:21][CH2:22][CH2:23]Cl)[CH3:20]>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:20][CH2:19][O:21][CH2:22][CH3:23])=[CH:4][C:3]=1[CH3:10]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 4-bromo-3,5-dimethylphenol (12 g, 59.7 mmol), potassium iodide (1.5 g, 9.0 mmol) and potassium carbonate (9.9 g, 71.6 mmol) in N,N-dimethylformamide (80 mL) was added 2-chloroethyl ethyl ether (9.7 g, 89.3 mmol) at room temperature with stirring and the mixture was stirred at 70° C. for 2 days. The reaction mixture was cooled and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=19/1) to give the title compound (15.9 g, yield 98%) as a yellow oil.
Aufarbeitung
- stirringthe mixture was stirred at 70° C. for 2 days
- temperatureThe reaction mixture was cooled
- concentrationconcentrated under reduced pressure
- customThe residue was partitioned between ethyl acetate and water
- washThe organic layer was washed with saturated brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=19/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-d36509fef7d647219d495960856c54a5
- Quelldatensatz
- uspto-grants-2008_11
- Patentnummer
- US07456218B2
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