Reaktion #592701

Reaktionsgleichung

ammonium chloride

2,3-dichloronitrobenzene

3-bromo-5-chlorophenol

potassium carbonate

→

title compound

2-(3-bromo-5-chlorophenoxy)-1-chloro-3-nitrobenzene

Lösungsmittel

NMP

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeplaced in an oil bath at 120° C
2. 2
   Extraktionthe mixture was extracted with ethyl acetate (2×50 mL)
3. 3
   WaschenThe combined organic fractions were washed with dilute brine (4×50 mL)
4. 4
   Trocknendried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe solvent was evaporated under reduced pressure
7. 7
   SonstigeThe residue was purified by automated column chromatography on silica gel (80 g)
8. 8
   Wascheneluting with 0-100% CH2Cl2/hexanes

Vorschrift

2,3-dichloronitrobenzene (764 mg, 3.99 mmol), 3-bromo-5-chlorophenol (1.65 g, 7.98 mmol) and potassium carbonate (661 mg, 4.79 mmol) were suspended in NMP (5 mL) and placed in an oil bath at 120° C. After 2 hours, the reaction was allowed to cool to room temperature, saturated aqueous ammonium chloride (10 mL) was added and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic fractions were washed with dilute brine (4×50 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by automated column chromatography on silica gel (80 g), eluting with 0-100% CH2Cl2/hexanes to yield the title compound. 1H NMR (CD3CN) δ 8.02 (dd, J=8.3 Hz, J=1.5 Hz, 1H), 7.88 (dd, J=8.2 Hz, J=1.6 Hz, 1H), 7.52 (dd, J=8.2 Hz, J=8.3 Hz, 1H), 7.38 (m, 1H), 7.07 (m, 1H), 6.97 (m, 1H).

Quelle