Reacción #88151

Ecuación de reacción

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

Rendimiento 33.4%

Disolventes

water

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was cooled
2. 2
   Extracciónextracted three times with EtOAc
3. 3
   SecadoThe organic layers were dried over anhydrous sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   OtroPurification by flash chromatography (0-50% EtOAc/hexanes)

Procedimiento

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]+).

Fuente