Reaktion #88151

Reaktionsgleichung

2-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazole

methyl 4-iodobenzoate

1,10-phenanthroline

cesium carbonate

→

methyl 4-(5-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazol-2-yl)benzoate

Ausbeute 33.4%

Lösungsmittel

water

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled
2. 2
   Extraktionextracted three times with EtOAc
3. 3
   TrocknenThe organic layers were dried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   SonstigePurification by flash chromatography (0-50% EtOAc/hexanes)

Vorschrift

A mixture of 2-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazole (2.186 g, 7.80 mmol), methyl 4-iodobenzoate (3.07 g, 11.70 mmol), copper(I) iodide (0.28 g, 1.47 mmol), 1,10-phenanthroline (0.30 g, 1.67 mmol), and cesium carbonate (2.54 g, 7.80 mmol) in anhydrous DMSO (20 mL) was heated at 100° C. for 18 hours. The reaction was cooled, diluted with water, and extracted three times with EtOAc. The organic layers were dried over anhydrous sodium sulfate, filtered, and adsorbed onto silica gel. Purification by flash chromatography (0-50% EtOAc/hexanes) provided methyl 4-(5-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazol-2-yl)benzoate as a white solid (1.08 g, 33%): mp 185-191° C.; 1H NMR (400 MHz, CDCl3) δ 8.25-8.19 (m, 6H), 7.41 (t, J=9.4 Hz, 2H), 3.98 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −85.96, −85.98, −87.79; ESIMS m/z 415 ([M+H]+).

Quelle