Adding a certain compound to certain chemical reactions, such as: 340825-13-0, name is 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 340825-13-0, Application In Synthesis of 6-Iodo-3,4-dihydronaphthalen-1(2H)-one
A solution of 6-iodo-3,4-dihydronaphthalen-1(2B)-one (5.0 g, 18.38 minol), 4- fluorobenzenethiol (4.11 mL, 38.6 minol) and absolute ethanol (20 mL) was cooled with an ice-water bath and bubbled with HC1 gas until saturation was reached (observed by theformation of a white precipitate). The mixture was allowed to warm to rt and stirred overnight. The mixture was dissolved in ether (250 mL) and washed sequentially with water (2 x 125 mL), 0.5 M aqueous Na2CO3 (3 xlOO mL) and brine (100 mL). The organic layer was dried and concentrated to provide a solid (9.2 g) which was a mixture of thioketal and vinyl sulfide. The solid was dissolved in chloroform (150 mL) andcooled in an ice-water bath. A solution of mCPBA (35 g, 156 minol) in DCM (200 mL)was washed with brine (50 mL), dried, filtered, and the filter cake was washed with DCM(50 mL). The combined filtrates were added dropwise in portions to the chloroformsolution of the products from above until the reaction was completed as judged by LCMS(175 ml. of the mCPBA solution was needed). The mixture was cooled in an ice bath,filtered to remove the insoluble material, and the filtrate was stirred with 10% aqueousNa2S2O3 (120 mL) for 5 min. The organic phase was separated, washed sequentially with 10% aqueous Na2S2O3 (2 x 120 mL), 10% aqueous Na2CO3 (3 x 200 mL) and brine (150 mL), dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-20%) to give 4-((4- fluorophenyl)sulfonyl)-7-iodo-1,2-dihydronaphthalene (5.3 g, 70% yield) as a white foamy solid.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, and friends who are interested can also refer to it.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BATT, Douglas G.; DHAR, T.G. Murali; (146 pag.)WO2018/71314; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com