Synthetic Route of 328-73-4,Some common heterocyclic compound, 328-73-4, name is 1-Iodo-3,5-bis(trifluoromethyl)benzene, molecular formula is C8H3F6I, 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.
A 2-dram vial equipped with a magnetic stir bar was charged with the amide substrate (36.5 mg, 0.10 mmol), Pd(OAc)2 (2.2 mg, 10 molpercent) , ligand L19 (4.1 mg, 20 molpercent), AgOAc (50 mg, 0.30 mmol) and norbornene (14.1 mg, 0.15 mmol). Aryl iodide (0.30 mmol) and 1.0 mL of t-butyl methyl ether were then added to the mixture. The vial was capped and closed tightly. The mixture was stirred at 95 °C for 12 hours . After cooling to room temperature, the mixture was passed through a pad of Celite® with ethyl acetate as the eluent to remove all the insoluble compounds. The resulting solution was concentrated, and the residual mixture was dissolved with a minimal amount of acetone and loaded onto a preparative TLC plate. The pure product was then isolated by preparative TLC with ethyl acetate and hexanes as the eluent. 2- { 5- [2- (Me hoxycarbonyl) henyl] -2-methylphenyl } – N- [2 , 3 , 5 , 6-tetrafluoro-4- (trifluoromethyl) phenyl] – ace amide Preparative TLC using hexanes/EtOAc (4/1) as the eluent provided the pure product as a white solid (64percent yield). NMR (600 MHz, acetone-d6) delta 9.54 (br, 1H, N-H) , 7.75 (d, J = 7.6 Hz, 1H) , 7.59 (t, J = 7.6 Hz, 1H) , 7.46 (t, J = 7.6 Hz, 1H) , 7.44 (d, J = 7.6 Hz, 1H) , 7.30 (d, J = 1.4 Hz, 1H) , 7.27 (d, J = 7.7 Hz, 1H) , 7.17 (dd, J = 7.7, 1.4 Hz, 1H) , 3.97 (s, 2H) , 3.60 (s, 3H) , 2.41 (s, 3H) ; 13C NMR (150 MHz, acetone-d6) delta 169.70, 169.43, 142.44, 139.82, 137.14, 134.19, 132.37, 132.01, 131.35, 131.26, 130.96, 130.31, 128.03, 127.96, 52.15, 41.17, 19.40. HRMS (ESI-TOF) m/z Calcd for C24Hi7F7N03+ [M+H] + 500.1091, found 500.1090. 6 Equivalents of Arl was used, and AgOAc was replaced by AgOPiv (3 eq. ) in this reaction. Column chromatography using hexanes/EtOAc (4/1) as the eluent provided the pure product as a white solid (76percent yield). XH NMR (400 MHz, acetone-d6) delta 9.62 (br, 1H, N-H) , 8.28 (s, 2H) , 8.02 (s, 1H) , 7.86 (d, J = 2.0 Hz, 1H) , 7.71 (dd, J = 8.0, 2.0 Hz, 1H) , 7.40 (d, J = 8.0 Hz, 1H) , 4.06 (s, 2H) , 2.44 (s, 3H) ; 13C NMR (150 MHz, acetone-d6) delta 169.33, 144.09, 139.45, 136.35, 135.64, 132.65 (q, J = 33.0 Hz), 132.08, 130.11, 127.93, 127.00, 124.54 (q, J = 270.0 Hz), 121.43 (m) , 41.20, 19.40. HRMS (ESI-TOF) m/z Calcd for C24Hi3F13 O+ [M+H]+ 578.0784, found 578.0785.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-3,5-bis(trifluoromethyl)benzene, its application will become more common.
Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; YU, Jin-Quan; (107 pag.)WO2016/123361; (2016); A1;,
Iodide – Wikipedia,
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