Application of 2043-57-4,Some common heterocyclic compound, 2043-57-4, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane, molecular formula is C8H4F13I, 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 an Ar atmosphere, BuLi (7.3 mL, 19.0 mmol, 2.6 M in hexanes) was added to a THF solution (50 mL) of iPr2NH (0.81 mL, 11.3 mmol) at -78 C and stirred for 20 min at the same temperature. The reaction mixture was stirred for 30 min at 0 C and then cooled to -78 C. A THF solution (30 mL) of 4,4′-dimethyl-2,2′-bipyridine (0.92 g, 5.0 mmol) was added and stirred for 3 h at the same temperature, and then 3-(perfluorohexyl)ethyl iodide (4.8 g, 10.2 mmol) was added. The reaction mixture was stirred at -78 C for 1 h and stirred at room temperature overnight. The mixture was diluted with brine and extracted with Et2O (30 mL¡Á3). The organic layer was dried over Na2SO4 and the solvent was removed under the reduced pressure. The residue was purified by recrystallization from MeOH to give ligand II (0.53 g, 12%) as brown scales. Mp 112-115 C; 1H NMR (400 MHz, CDCl3/TMS) delta (ppm): 2.02-2.19 (m, 8H), 2.82 (t, 4H, J=7.8 Hz), 7.17 (dd, 2H, J=5.3, 1.7 Hz), 8.28 (s, 2H), 8.61 (d, 2H, J=5.3 Hz); 13C{1H} NMR (100 MHz, CDCl3/TMS) delta (ppm): 21.0, 30.4 (t, J=22.2 Hz), 34.6, 121.1, 123.8, 149.3, 150.6, 156.3; LRMS (EI) m/z: 876 (M+); HRMS: calcd for C28H18F26N2: 876.1055, found: 876.1044; IR (neat): 3800, 3674, 3587, 3438, 2194, 2157, 1962, 1651, 1107, 843 cm-1.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane, its application will become more common.
Reference:
Article; Inamoto, Kiyofumi; Nozawa, Kanako; Kadokawa, Jun; Kondo, Yoshinori; Tetrahedron; vol. 68; 38; (2012); p. 7794 – 7798;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com