Application of 34270-90-1,Some common heterocyclic compound, 34270-90-1, name is 1-Iodo-2-(2-iodoethoxy)ethane, molecular formula is C4H8I2O, 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 bis(trimethylsilyl)amide solution in THF (1M, 19.5 mL, 19.5 mmol) was added dropwise to a solution of 2-(4-bromo-2-methylphenyl)acetonitrile (3.75 g, 17.85 mmol) in THF (90 mL) at 0C. After stirring for 0.5 h, the cooling bath was removed and the reaction mixture was stirred at 20C for 0.5 h. l-Iodo-2-(2-iodoethoxy)ethane (2.8 mL, 19.67 mmol) was added dropwise. The reaction mixture was stirred for 0.5 h at 20C. Sodium bis(trimethylsilyl)amide solution in THF (1M, 19.5 mL, 19.5 mmol) was added dropwise. The reaction mixture was stirred for 18 h at 20C, then quenched with saturated aqueous ammonium chloride solution (25 mL) and diluted with water (25 mL). The aqueous layer was extracted with EtOAc (3 x 50 mL). The combined organic extracts were washed with brine (50 mL) and dried over sodium sulfate, then filtered and concentrated in vacuo. The resulting brown oil was separated by flash column chromatography on silica, using a gradient of fc/7-butyl methyl ether in heptane (0-25%), to afford the title compound (2.3 g, 45%) as a yellow solid. 6n (250 MHz, CDCb) 7.47- 7.36 (m, 2H), 7.16 (d, 8.4 Hz, 1H), 4.16-4.06 (m, 2H), 4.06-3.91 (m, 2H), 2.65 (s, 3H), 2.33-2.21 (m, 2H), 2.17-1.99 (m, 2H). HPLC-MS (method 9): [M+water]+ m/z 297 and 299, RT 1.80 minutes.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-2-(2-iodoethoxy)ethane, its application will become more common.
Reference:
Patent; UCB BIOPHARMA SRL; BRACE, Gareth Neil; BROOKINGS, Daniel Christopher; FOULKES, Gregory; LECOMTE, Fabien Claude; (0 pag.)WO2020/11731; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com