Some common heterocyclic compound, 118863-62-0, name is 3-(4-Bromophenyl)-1H-[1,2,4]triazole, molecular formula is C8H6BrN3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: Triazoles
Example 43 Preparation of 3-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C23) In a 500 mL flask, 3-(4-bromophenyl)-1H-1,2,4-triazole (20.0 g, 89.6 mmol), 1-iodo-4-(trifluoromethoxy)benzene (39.0 g, 135 mmol) were diluted with N,N-dimethylformamide and water (4:1, 100 mL). Then copper(I) iodide (15.3 g, 80.6 mmol), 8-hydroxyquinoline (8.50 g, 58.2 mmol) and cesium carbonate (87.4 g, 269 mmol) were added. The reaction was heated to 150 C. and stirred for 16 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and filtered through Celite. Brine solution was added to the filtrate and stirred for 15 minutes. The layers were separated and the aqueous layer further extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered, and concentrated. The resulting residue was purified by flash column chromatography using 15% ethyl acetate/petroleum ether as eluent to afford the title compound as a white solid (10.0 g, 29%): mp 100-103 C.; 1H NMR (300 MHz, DMSO-d6) delta 9.42 (s, 1H), 8.07 (d, J=9.0 Hz, 2H), 8.05 (d, J=9.0 Hz, 2H), 7.73 (d, J=8.4 Hz, 2H), 7.62 (d, J=8.4 Hz, 2H); ES+ m/z 385 ([M+H]+).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 118863-62-0, its application will become more common.
Reference:
Patent; Dow AgroSciences LLC; Baum, Erich W.; Fischer, Lindsey G.; Crouse, Gary D.; Sparks, Thomas C.; Giampietro, Natalie C.; Dent, III, William H.; Niyaz, Noormohamed M.; Petkus, Jeff; Demeter, David A.; Lambert, William Thomas; McLeod, CaSandra L.; Rigsbee, Emily Marie; Renga, James M.; (128 pag.)US2016/21883; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics