Pyridine → 6-Bromo-8-chloro-7-methoxy-2,2-dimethyl-chroman-4-one
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][C:7]([CH3:15])([CH3:14])[CH2:6][C:5]2=[O:16].S(Cl)([Cl:20])(=O)=O.N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:20])[C:11]=1[O:12][CH3:13])[O:8][C:7]([CH3:14])([CH3:15])[CH2:6][C:5]2=[O:16]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 6-bromo-7-methoxy-2,2-dimethyl-chroman-4-one (Compound 4, 2.80 g, 9.8 mmol) in methylene chloride (50 nL) at 0° C. were added sulfuryl chloride (1.59 g, 11.7 mmol) followed by treatment with pyridine (0.87 g, 11.7 mmol). After stirring at 0° C. and slow warning room temperature over 3 h, the reaction was quenched with ice water. The resulting mixture was extracted with dichloromethane and then the combined organic layers were washed with water and brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (silica gel, 95:5 hexane/ethyl acetate) to afford the title compound as a colorless oil.
Aufarbeitung
- customthe reaction was quenched with ice water
- extractionThe resulting mixture was extracted with dichloromethane
- washthe combined organic layers were washed with water and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude residue was purified by flash chromatography (silica gel, 95:5 hexane/ethyl acetate)
Quellen und Nachweise
- ORD-Eintrag
- ord-4df0d9a9f0e14c12863c46c1125b3857
- Quelldatensatz
- uspto-grants-2005_05
- Patentnummer
- US06887896B1
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