Electric Literature of 626-01-7,Some common heterocyclic compound, 626-01-7, name is 3-Iodoaniline, molecular formula is C6H6IN, 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: A round bottom flask was charged with 28 4-iodoaniline (5, 3g, 13.7mmol, 1.0 eqv.) and 29 water (15.2mL, 0.90M). 30 Concentrated HCl (2.5mL 2.1 eqv.) was added to vigorously stirred reaction mixture in an ice-water bath. A pre-cooled solution of 31 NaNO2 (0.95g, 13.7mmol, 1.0 eqv.) in water (5.50mL, 2.50M) was added dropwise to the reaction mixture, after which time the reaction mixture was stirred for 15min. The solution of 32 NaN3 (0.89g, 13.7mmol, 1.0 eqv.) in water (5.50mL 2.50M) was added dropwise to the reaction mixture while maintaining the temperature in the ice bath, and then the reaction mixture was stirred an additional 20min at 0C, then stirred at rt for another 3h. The reaction mixture was extracted with EtOAc (2×50mL) and the aqueous layer was adjusted to pH 8-10 with NaHCO3 before discarding. The combined organic solution was washed with water and brine and dried over Na2SO4, filtered and concentrated under reduced pressure. The crude azidoiodobenze derivative was further purified by flash column chromatography over silica gel with 0-5% ethylacetate/hexanes as eluent to afford 33 4-azidoiodobenze (7, 2.60g, 78%). 1H NMR (400MHz, CDCl3) delta 7.63 (d, J=8.7Hz, 2H), 6.77 (d, J=8.7Hz, 2H). 13C NMR (101MHz, CDCl3) delta 140.06, 138.79, 121.14, 88.31.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Iodoaniline, its application will become more common.
Reference:
Article; Hayes, Karen E.; Batsomboon, Paratchata; Chen, Wei-Chih; Johnson, Brennan D.; Becker, Andreas; Eschrich, Steven; Yang, Yan; Robart, Aaron R.; Dudley, Gregory B.; Geldenhuys, Werner J.; Hazlehurst, Lori A.; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1479 – 1488;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com