Application of 216393-67-8,Some common heterocyclic compound, 216393-67-8, name is 4-Chloro-2-fluoro-6-iodoaniline, molecular formula is C6H4ClFIN, 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.
In a 350 mL glass pressure vessel with a threaded Teflon cap, 4-chloro-2-fluoro-6-iodoaniline (3.25 g, 12.0 mmol), CuI (30 mg, 0.16 mmol), and Pd(PPh3)2Cl2 (0.101 g, 0.144 mmol) were taken up in 165 mL triethylamine and cooled to -78 C. Propyne (2.7 mL, 1.9 g, 48 mmol) was condensed into a graduated cylinder and added to the reaction vessel. The vessel was then capped, the cooling bath removed, and the reaction mixture allowed to stir while warming to room temperature overnight behind a safety shield. Removal of the triethylamine by evaporation gave a crude material that was purified by flash chromatography over silica gel (1-10% ethyl acetate in hexanes) to give pure product (2.00 g, 91% yield): 1H NMR (CHLOROFORM-d) delta 7.00-7.04 (m, 1H), 6.95 (dd, J=10.6, 2.3 Hz, 1H), 4.18 (br. s., 2H), 2.13 (s, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-2-fluoro-6-iodoaniline, its application will become more common.
Reference:
Patent; Wyeth, LLC; US2011/105509; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com