Electric Literature of 340825-13-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 340825-13-0, name is 6-Iodo-3,4-dihydronaphthalen-1(2H)-one belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
Alternative Procedure: A solution of 6-iodo-3,4-dihydronaphthalen-1(2H)-one (5.0 g, 18.4 mmol), 4-fluorobenzenethiol (4.1 mL, 38.6 mmol) and absolute ethanol (20 mL) was cooled on an ice-water bath and bubbled with HCl gas until saturation was reached (observed by the formation of a white precipitate). The mixture was allowed to warm to rt and stirred overnight. The mixture was dissolved in diethyl ether (250 mL) and washed sequentially with water (2*125 mL), 0.5 M aqueous Na2CO3 (3*100 mL) and brine (100 mL). The organic layer was dried and concentrated to provide a solid (9.20 g) which was a mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane). The solid was dissolved in chloroform (150 mL) and cooled in an ice-water bath. A solution of mCPBA (35.0 g, 156 mmol) in DCM (200 mL) was washed with brine (50 mL), dried over Na2SO4, filtered, and the filter cake was washed with DCM (50 mL). The combined filtrates were added dropwise in portions to the chloroform solution of the mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane) 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% aqueous Na2S2O3 (120 mL) for 5 min. The organic phase was separated, washed sequentially with 10% aqueous Na2S2O3 (2*120 mL), 10% aqueous Na2CO3 (3*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 amorphous solid.
The synthetic route of 6-Iodo-3,4-dihydronaphthalen-1(2H)-one has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Marcoux, David; Beaudoin Bertrand, Myra; Dhar, T.G. Murali; Yang, Michael G.; Xiao, Zili; Xiao, Hai-Yun; Zhu, Yeheng; Weigelt, Carolyn A.; Batt, Douglas G; (154 pag.)US2018/127368; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com