Application of 75581-11-2,Some common heterocyclic compound, 75581-11-2, name is 4-Iodo-1-methoxy-2-methylbenzene, molecular formula is C8H9IO, 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.
A mixture of 1,4-dioxa-spiro[4,5]dec-7-en-8-boronic acid pinacol ester (25.0 g, 93.9 mmol), 4-iodo-2-methylanisole (28.0 g, 113 mmol), 1,1?-bis(diphenylphosphino)ferrocenedichlorlopalladium(II) (1.38 g, 1.89 mmol), dioxane (470 mL) and 1MNa2CO3 (282 mL, 282 mmol) was degassed with 3 vacuum/N2 cycles, stirred at 50 C for 2.5 h, and then allowed to cool to a The mixture was diluted with ethyl acetate (500 mL) and washed with saturated NaHCO3 (500 mL x 2). The aqueous layers were back extracted with ethyl acetate (200 mL). The combined ethyl acetate extracts were dried (Na2SO4), filtered, concentrated and purified by silica gel chromatography (0-5% ethyl acetate in hexanes) to give 8-(4-methoxy-3-methylphenyl)-1,4- dioxaspiro[4.5]dec-7-ene (19.9 g, 81%). ?H NMR (400 MHz, DMSO-d6): 7.21-7.16 (m, 2H), 6.85 (d, 1H), 5.89-5.84 (m, 1H), 3.90 (s, 4H), 3.76 (s, 3H), 2.52-2.47 (m, 2H), 2.32 (br s, 2H),2.13 (s, 3H), 1.77 (t, 2H); MS: 261.1 [M+H].
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodo-1-methoxy-2-methylbenzene, its application will become more common.
Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; (192 pag.)WO2017/49177; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com