Electric Literature of 103440-52-4,Some common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, molecular formula is C9H9IO2, 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.
General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuI (10 mg, 0.05 mmol, 10 mol%), K2CO3 (276 mg, 2.0 mmol), 1,10-phenanthroline (20 mg, 0.10 mmol, 20 mol%) and cyclic thiourea (0.5 mmol), 4 ? Molecular Sieves. The tube was evacuated and backfilled with N2 (this procedure was repeated 3 times). Under a counter flow of N2, methyl-2-iodobenzoate 1 (0.6 mmol) and DMF (2.0 mL) were added by syringe. The mixture was stirred at 100 ºC for 24h. After the reaction was completed, the mixture was directly passed through celite and rinsed with 30 mL of EtOAc. The combined filtrate was concentrated and purified by column chromatography on silica gel to give the pure product.Yellow Yellow solid; mp 126-128 C; 1H NMR (400 MHz, CDCl3) delta 8.04 (s, 1H), 7.31 (d, J = 7.6 Hz,1H), 7.12 (d, J = 8.0 Hz,1H), 3.52-3.45 (m, 1H), 3.28-3.22 (m, 1H), 3.12-3.09 (m, 1H), 2.38-2.36 (m, 4H), 1.91 (s, 2H), 1.72-1.63 (m, 1H), 1.56-1.43 (m, 3H); 13C NMR (50 MHz, CDCl3) delta 162.5, 154.8, 137.0, 134.5, 130.9, 128.6, 125.2, 124.5, 71.7, 67.5, 31.1, 30.9, 25.4, 25.0, 21.1 ppm. Anal. Calcd. for C15H16N2OS: C 66.15, H 5.92, N 10.29; found: C 66.21, H 5.70, N 10.37; EI-MS: m/z = 272 (M+).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-Iodo-5-methylbenzoate, its application will become more common.
Reference:
Article; Chen, Dingben; Wu, Jiashou; Yang, Jianguo; Huang, Ling; Xiang, Yubo; Bao, Weiliang; Tetrahedron Letters; vol. 53; 52; (2012); p. 7104 – 7107;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com