Application of 51628-12-7, 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. 51628-12-7, name is 2-(4-Iodophenyl)acetonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
EXAMPLE 26 Preparation of 2-{4-[4-(1-Methyl-2-{[(methylethyl)sulfonyl]amino}ethoxy)phenyl]phenyl}ethanenitrile. Preparation of 4-(cyanomethyl-phenylboronic acid, pinacol ester. Using the method of Murata, M., et al., Y. J. Org. Chem, 62 6458-6459 (1997), 4-iodophenylacetonitrile (23.9 g, 0.100 mol), Et3N (42 ML, 0.30 mol), acetonitrile (400 ML) and Pd(dppf)2Cl2 catalyst ([1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2) were combined in a 1 L flask and the resulting solution was evacuated and purged with nitrogen three times.The pinacolborane (22 ML, 0.15 mol) was added and the mixture was heated at reflux for 3 h. 1H NMR analysis of an aliquot indicated complete consumption of starting 4-iodophenylacetonitrile.The mixture was cooled to room temperature, concentrated to an oil and taken up in CH2Cl2.This solution was extracted with 0.1 N HCl (3*100 ML) and the organic phase was separated, concentrated and re-dissolved in methyl tert-butyl ether (MTBE).The MTBE solution was passed through a filter packed with silica gel (300 g).The eluant was concentrated to a dark red oil.This oil was extracted with hexanes (500 ML) and the soluble fraction was decanted away from a black oil (5 g). MTBE (5 ML) was added to this oil to give a suspension that was filtered through Celite.This filtrated was combined with the hexanes fraction and the solution was concentrated to an oil.Finally, the oil was re-dissolved in di-isopropyl ether (150 ML) and was diluted with hexanes (400 ML).This mixture was allowed to stand for 2 h, and then filtered to remove a dark precipitate.The resulting amber filtrate was concentrated to an oil, re-dissolved in hexanes (400 ML) and concentrated to 75 ML without added heat.This treatment resulted in the precipitation of the desired intermediate title compound as a golden waxy solid that was air-dried to afford 23.0 g (96.2%): 1H NMR (CDCl3, 300 MHz): delta7.8 (d, 2H); 7.35 (d, 2H); 3.8 (s, 2 H) 1.15 (s, 12H).
The synthetic route of 2-(4-Iodophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Davison, Joshua Zwick; Jones, Winton Dennis; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael; US2003/225266; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com