Synthetic Route of 345226-19-9,Some common heterocyclic compound, 345226-19-9, name is 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene, molecular formula is C7H3ClF3IO, 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.
To a mixture of 8-{[tert-butyl(dimethyl)silyl]oxy}-2-azaspiro[4.5]decan-1 -one (500 mg, 1 .76mmol) (isomer 1) and 3-chloro-4-iodophenyl trifluoromethyl ether (696 mg, 98% purity, 2.12mmol) in o-xylol (38 ml) was added under an argon atmosphere copper(l) iodide (67.2 mg, 353 pmol), N,N?-dimethylethylenediamine (77 pI, 710 pmol) and potassium phosphate (749 mg, 3.53 mmol) and the reaction was heated to 1400 for 48 h in a microwave reactor. Upon cooling, the reaction mixture was filtrated through a pad of celite the residue was washedwith ethyl acetate and the filtrate was concentrated under reduced pressure. Another batch was prepared accordingly, the batches were combined and the crude product was purified by flash chromatography (hexanes/ethyl acetate-gradient, 50% -> 100% ethyl acetate) to give the title compound as single isomer (1.0 g). [C-MS (Method 2): R = 1.78 mm; MS (ESipos): m/z = 478 [M+H]1H-NMR (400 MHz, DMSO-d6): 6 [ppm] = 7.71 (d, 1H), 7.62-7.36 (m, 2H), 3.94 (br 5, 1H),3.62 (t, 2H), 2.07 (t, 2H), 2.01-1.83 (m, 2H), 1.71-1.54 (m, 4H), 1.33 (brd, 2H), 0.88 (s, 9H),0.05 (s, 6H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene, its application will become more common.
Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
Iodide – Wikipedia,
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