Application of 501433-06-3,Some common heterocyclic compound, 501433-06-3, name is 2,3-Difluoro-1,4-diiodobenzene, molecular formula is C6H2F2I2, 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.
Under nitrogen atmosphere, 2,3-difluoro-1,4-diiodobenzene (7, 430 mg, 1.18 mmol), bis-(triphenylphospino)dichloropalladium(II) (85.1 mg, 121 mumol) and copper(I) iodide (23.2 mg,122 mumol) were dissolved in anhydrous THF (20 mL) and triethylamine (20 mL).Trimethylsilylacetylene (0.41 mL, 2.96 mmol) was added and the solution stirred at 70 C for16 h. Subsequently, the reaction mixture was filtered through a bed of Celite, the solvent wasevaporated in vacuo and the crude product purified by column chromatography using silicaand n-hexane as eluent (Rf = 0.44) to obtain a colourless solid (332 mg, 1.08 mmol, 92%).Melting point: 78 C;1H NMR (500MHz, CDCl3, 300 K): delta = 7.12-7.10 (m, 2H) ppm;13C NMR (125 MHz, CDCl3, 300 K): delta = 151.4 (dd, 1JC,F = 255.9 Hz, 2JC,F = 15.0 Hz, 2C), 127.9 (mc,2C), 114.2 (mc, 2C), 103.7 (mc, 2C), 96.4 (mc, 2C), 0.1 (6C) ppm.IR (ATR): = 2960 (w), 2900 (w), 2165 (m), 1549 (w), 1489 (m), 1466 (s), 1310 (w), 1249 (s),1228 (m), 1170 (w), 1044 (m), 963 (s), 838 (vs), 817 (vs), 758 (vs), 702 (s) cm-1;MS (EI, 70 eV): m/z (%) = 306 (45) [M]+, 293 (100) [M-Me]+, 112 (41) [M-2I]+;HR-MS (EI, 70 eV): m/z = calcd. for C16H20F2Si2 [M]+ 306.1072, found 306.1072.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Difluoro-1,4-diiodobenzene, its application will become more common.
Reference:
Article; Hamer, Sebastian; Roehricht, Fynn; Jakoby, Marius; Howard, Ian A.; Zhang, Xianghui; Naether, Christian; Herges, Rainer; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1331 – 1338;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com