Application of 52107-68-3, These common heterocyclic compound, 52107-68-3, name is 5-Iodo-2-methylbenzonitrile, 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.
A stirred slurry of sodium hydride (60% dispersion in mineral oil, 480 mg, 12.0 mmol) in DME (3.0 mL)was refluxed. 5-iodo-2-methylbenzonitrile (729 mg, 3.00 mmol), methyl benzoate (544 mg, 4.00 mmol),and DME (3.0 mL) were added to the slurry. After a catalytic amount of MeOH was added, the mixture was refluxed for 7 h. The mixture was cooled to 0C. water (10 mL) was added to quench the reactionand then 2 M HCl (10 mL) was added. The resulting mixture was diluted with EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, and filtered. The solvents were evaporated in vacuo. The crude product was purified by recrystallization from ethanol to give 5-iodo-2-(2-oxo-2-phenylethyl)benzonitrile (5g)(635 mg, 61%). Yellow white solid. Mp 134-136C. 1H NMR (400 MHz, CDCl3): delta = 7.98-8.04 (m, 3H),7.87-7.89 (m, 1H), 7.60-7.64 (m, 1H), 7.49-7.53 (m, 2H), 7.10-7.13 (m, 1H), 4.49 (s, 2H). 13C NMR (100MHz, CDCl3): delta = 194.7, 141.8, 140.8, 138.1, 136.0, 133.8, 132.6, 128.8, 128.3, 116.3, 115.6, 91.7, 43.2.IR (KBr): 3097, 3056, 3033, 2951, 2884, 2230, 1688, 1594, 1479, 1448, 1416, 1385, 1332, 1204, 1110,988, 906, 868, 837, 806, 752 cm-1. HRMS (EI): Calcd for C15H10INO 346.9807 (M)+, found 346.9820.
Statistics shows that 5-Iodo-2-methylbenzonitrile is playing an increasingly important role. we look forward to future research findings about 52107-68-3.
Reference:
Article; Yashiro, Kai; Sakata, Keito; Hachiya, Iwao; Shimizu, Makoto; Heterocycles; vol. 92; 11; (2016); p. 2032 – 2046;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com