Electric Literature of 628-77-3,Some common heterocyclic compound, 628-77-3, name is 1,5-Diiodopentane, molecular formula is C5H10I2, 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.
Sodium hydride (9.73 mg, 0.243 mmol, 60%> suspension in mineral oil) was added to a solution of l ,3-difluoro-2-(((l ,l ,l ,3,3,3-hexafluoro-2-(4-(((4- fluorophenyl)sulfonyl)methyl)phenyl)propan-2-yl)oxy)methyl)benzene (13.2 mg, 0.024 mmol) and 1 ,5-diiodopentane (31.5 mg, 0.097 mmol) in Nu,Nu-dimethylformamide (1 mL). After 1 h at room temperature, LCMS analysis showed that the reaction was complete. The mixture was quenched with water (1 mL), diluted with ether (10 mL), washed with water (2×10 mL), brine (5 mL), dried (magnesium sulfate), filtered and concentrated under reduced pressure. The crude material was purified via preparative LC/MS with the following conditions: Column: Waters XBridge C18, 19 x 150 mm, 5-muiotaeta particles; Guard Column: Waters XBridge C I 8, 19 x 10 mm, 5-muiotaeta particles; Mobile Phase A: 5 :95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95 :5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 60-100% B over 15 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give Example 1 (9.0 mg, 57% yield). LC/MS (M+18): 628.1 ; LC retention time: 3.130 min (analytical HPLC Method C); 1H NMR (500 MHz, 1 : 1 mixture of CDC13-CD30D) delta ppm 7.66 – 7.58 (m, 2H), 7.49 – 7.38 (m, 3H), 7.30 – 7.21 (m, 2H), 7.08 – 6.95 (m, 4H), 4.73 (s, 2H), 2.66 (d, J=12.9 Hz, 2H), 2.26 (td, J=13.3, 3.2 Hz, 2H), 1.83 (d, J=13.4 Hz, 2H), 1.67 (d, J=12.4 Hz, 1H), 1.47 – 1.34 (m, 1H), 1.28 (q, J=13.0 Hz, 2H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,5-Diiodopentane, its application will become more common.