Reaktion #592742

Reaktionsgleichung

3-fluoro-4-methylpyridine-2-carbonitrile

3-bromo-5-chlorophenol

cesium carbonate

→

title compound

3-(3-bromo-5-chlorophenoxy)-4-methylpyridine-2-carbonitrile

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat 80° C. for another hour
2. 2
   Sonstigeafter which the mixture was partitioned between water (300 mL) and ethyl acetate (2×500 mL)
3. 3
   WaschenThe combined extracts were washed with water (100 mL)
4. 4
   Trocknenbrine (100 mL), dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe solvent removed in vacuo
7. 7
   SonstigeThe residue was chromatographed
8. 8
   Wascheneluted with a gradient of 0-10% EtOAc/CH2Cl2
9. 9
   Einengenconcentrated on the rotary evaporator

Vorschrift

A mixture of 3-fluoro-4-methylpyridine-2-carbonitrile (2.1 g, 15.43 mmol), 3-bromo-5-chlorophenol (3.68 g, 17.74 mmol) and cesium carbonate (5.03 g, 15.43 mmol) in DMF (30 mL) was heated at 70° C. for 1 hour and then at 80° C. for another hour, after which the mixture was partitioned between water (300 mL) and ethyl acetate (2×500 mL). The combined extracts were washed with water (100 mL) and then brine (100 mL), dried over MgSO4, filtered, and the solvent removed in vacuo. The residue was chromatographed using RediSep column (330 g) and eluted with a gradient of 0-10% EtOAc/CH2Cl2 and the pure fractions combined and concentrated on the rotary evaporator to give the title compound. LRMS (M+1)=324.9.

Quelle