5326-39-6, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 5326-39-6, name is 1-Iodo-4-methyl-2-nitrobenzene, A new synthetic method of this compound is introduced below.
General procedure: To a mixture of 3-bromo-2-nitrotoluene 15c (2.13g, 9.86mmol) and 1,4-dioxane (50mL) were added 2-imidazolidone 16a (4.01g, 46.6mmol), Cs2CO3 (4.71g, 14.5mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3; 400mg, 0.437mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (XantPhos; 503mg, 0.869mmol) under argon atmosphere. The mixture was stirred at 100C for 19.5h. After cooling to room temperature, the mixture was filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 0-5% MeOH in CHCl3), and concentrated in vacuo. To a mixture of the residue in EtOH (12mL) and H2O (3.0mL) were added FeCl3¡¤6H2O (99.0mg, 0.366mmol), N2H4¡¤H2O (1.10mL, 22.7mmol), and activated carbon (102mg). The mixture was stirred under reflux for 14h. After cooling to room temperature, the mixture was filtered through a pad of Celite. The filtrate was diluted with EtOAc, and washed with H2O and brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. A mixture of the residue and POCl3 (2.00mL, 21.8mmol) was stirred at 100C for 5h. After cooling to room temperature, the reaction mixture was concentrated in vacuo. 1M NaOH aqueous solution was added to the residue followed by extraction with CHCl3/MeOH co-solvent. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 0-3% MeOH in CHCl3) to give 17c (345mg, 20% in 3 steps) as a brown solid.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Chino, Ayaka; Honda, Shugo; Morita, Masataka; Yonezawa, Koichi; Hamaguchi, Wataru; Amano, Yasushi; Moriguchi, Hiroyuki; Yamazaki, Mayako; Aota, Masaki; Tomishima, Masaki; Masuda, Naoyuki; Bioorganic and Medicinal Chemistry; vol. 27; 16; (2019); p. 3692 – 3706;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com