Synthetic Route of 628-21-7,Some common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, molecular formula is C4H8I2, 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 solution of bis(oxazoline) 2l51 (0.100 g, 0.280 mmol) in THF (5 mL) were added TMEDA (73 muL, 0.56 mmol) and i-Pr2NH (39 muL, 0.28 mmol). The resulting mixture was then cooled at -78 C. n-BuLi (0.370 mL of a 2.5 M solution in hexanes, 0.56 mmol) was added via syringe to the cold mixture. The reaction mixture was warmed to -20 C and stirred for 20 min. The solution was cooled to -78 C and freshly distilled 1,4-diiodobutane (50 muL, 0.38 mmol) was added. After the addition, the cooling bath was removed and the mixture was allowed to stir at room temperature for 16 h. The mixture was quenched with saturated aqueous NH4Cl solution (1 mL) and diluted with water (1 mL). The resulting mixture was extracted with Et2O (2×5 mL). The combined organic layers were washed with brine (5 mL), dried over Na2SO4, and concentrated under reduced pressure to afford a dark orange oil. The desired bis(oxazoline) 2j was obtained as a white solid (87 mg, 75% yield) after flash chromatography (50% EtOAc/hexanes). Rf 0.58 (50% EtOAc/hexanes); [alpha]D25 -108.8 (c 0.50, CHCl3); mp 79-81 C; 1H NMR (400 MHz, CDCl3) delta 7.72 (d, J=8.7 Hz, 2H), 7.40 (dd, J=7.2, 2.1 Hz, 2H), 7.08-7.01 (m, 3H), 6.67 (d, J=8.7 Hz, 2H), 6.50 (s, 1H), 2.99 (dd, J=6.4, 3.6 Hz, 1H), 2.17 (d, J=6.3 Hz, 1H), 1.64 (d, J=3.5 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 160.3, 147.7, 143.6, 132.3, 129.9, 129.5, 128.0, 127.1, 123.9, 99.0, 84.4, 38.7, 35.7; IR (neat) 2955, 2924, 2856, 1741, 1603, 1515, 1346, 1323, 1305, 1288, 1222, 1181, 1136, 1019, 948, 787, 748, 698 cm-1; HMRS (ESI) calcd for C27H33N2O2 [M+H]+: 417.25365; found: 417.25428.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Diiodobutane, its application will become more common.
Reference:
Conference Paper; Lebel, Helne; Parmentier, Michael; Leogane, Olivier; Ross, Karen; Spitz, Cedric; Tetrahedron; vol. 68; 17; (2012); p. 3396 – 3409;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com