Electric Literature of 69113-59-3, These common heterocyclic compound, 69113-59-3, name is 3-Iodobenzonitrile, its 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.
General procedure: In a typical experiment Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.1mg, 0.05mmol), iodobenzene (1) (or an other iodoaromatics, 2-18) (1.0mmol), and 2-amino-1,3,4-thiadiazol (a) (or its 5-substituted derivatives, b or c, or 2-amino-1,3-thiazole, d) (121.4mg, 1.2mmol) and triethylamine (0.5mL) were dissolved in DMF (10mL) under argon in a 100mL three-necked flask equipped with reflux condenser connected to a balloon filled with argon. The atmosphere was changed to carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 70C and analyzed by TLC and GC-MS. The cooled reaction mixture was then concentrated and evaporated to dryness under reduced pressure. (0025) Method A. (2a, 14a, 1d-8d, 10d, 14d-16d): The residue was dissolved in chloroform (15mL) and washed three times with water (30mL). The organic phase was dried over Na2SO4, filtered and evaporated under reduced pressure to a solid material. Aforesaid compounds were subjected to column chromatography (Silicagel 60 (Merck), 0.063-0.200mm), EtOAc/CHCl3 eluent mixtures (the exact ratios are specified in Characterization for each compound; isolated yields are not optimized). (0026) Method B. (1a, 3a-13a, 15a-17a, 1b, 2b, 13b, 1c, 2c, 9d, 11d-13d, 17d): Toluene (15mL) was added to the residue, the insoluble material (product) was filtered, washed with water on the filter and dried. The off-white powder-like material was dissolved in methanol, the palladium-black was filtered off and methanol was evaporated.
The synthetic route of 69113-59-3 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Gergely, Mate; Kollar, Laszlo; Tetrahedron; vol. 74; 16; (2018); p. 2030 – 2040;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com