8-Hydroxyquinoline → 1-(4-(perfluoropropyl)phenyl)-3-(p-tolyl)-1H-1,2,4-triazole

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Heptafluoropropyl-1-iodopropane (3.14 g, 10.6 mmol), 1-iodo-4-bromobenzene (2.0 g, 7.07 mmol), and copper (powder: 1.123 g, 17.7 mmol) were combined in 16 mL of DMSO in a 20 mL microwave tube, and the solution was stirred and heated at 175° C. for 90 min. The cooled solution was then extracted with 2×30 mL of hexanes, and the combined organic layer was washed with water, dried and concentrated to give 2.0 grams of a yellow oil. This crude material, which consisted of a mixture of 4-heptafluoropropyl-iodobenzene and 4-heptafluoropropyl-bromobenzene, was combined with 3-(p-tolyl)-1H-1,2,4-triazole (1.0 g, 6.28 mmol), cesium carbonate (6.14 g, 18.9 mmol), CuI (0.12 g, 0.63 mmol), and quinolin-8-ol (0.091 g, 0.63 mmol) in 16 mL of 90:10 DMF-water, and the solution was heated to 125° C. for 8 hrs. The cooled solution was then poured onto 60 mL of a 2N aqueous NH4OH solution, and the resulting precipitate was filtered and air-dried. This material was heated in 50 mL of MeOH, filtered, and the filtrate diluted with 30 mL of water. The resulting solid was filtered and air-dried to give 1-(4-(perfluoropropyl)phenyl)-3-(p-tolyl)-1H-1,2,4-triazole as a white solid (1.03 g, 39%): mp 140-143° C.; 1H NMR (400 MHz, CDCl3) δ 8.66 (s, 1H), 8.10 (d, J=8.1 Hz, 2H), 7.94 (d, J=8.9 Hz, 2H), 7.76 (d, J=8.5 Hz, 2H), 7.30 (dt, J=8.0, 0.7 Hz, 2H), 2.43 (s, 3H); ESIMS m/z 405 ([M+H]+).

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