These common heterocyclic compound, 2571-52-0, name is 2,4,6-Trimethylbenzonitrile, 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. 2571-52-0
Example 32: Synthesis of 2- [4- (5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2- trifluoromethylpentyl]-4, 6-dimethylbenzonitrile and 4- [4- (5-fluoro-2-methoxyphenyl)-2- hydroxy-4-methyl-2-trifluoromethylpentyl]-2, 6-dimethylbenzonitrile The title compounds were prepared as an inseparable mixture by methods analogous to those described in Example 5 as a result of performing a Grignard reaction with a 1: 1.4 mixture of 2- bromomethyl-4,6-dimethylbenzonitrile and 4-bromomethyl-2,6-dimethylbenzonitrile (prepared by N bromosuccinimide bromination of 2, 4, 6-trimethylbenzonitrile) The mixture was treated with boron tribromide according to methods analogous to those described in Example 7 followed by chromatography on a prep plate (silica gel, hexanes-isopropyl alcohol (97: 3,2X developed) ) to afford 2- [4- (5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2- trifluoromethylpentyl]-4, 6-dimethylbenzonitrile, m. p. 136C-138C, and 4- [4- (5-fluoro-2- hydroxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2, 6-dimethylbenzonitrile, m. p. 152C-154C. Methylation of 2- [4- (5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2- trifluoromethylpentyl]-4, 6-dimethylbenzonitrile and 4- [4- (5-fluoro-2-hydroxyphenyl)-2- hydroxy-4-methyl-2-trifluoromethylpentyl] -2,6-dimethylbenzonitrile by analogous methods described in Example 8 gave the title compounds 2- [4- (5-fluoro-2-methoxyphenyl)-2-hydroxy- 4-methyl-2-trifluoromethylpentyl]-4, 6-dimethylbenzonitrile, m. p. 134C-136C, and 4- [4- (5- fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2, 6- dimethylbenzonitrile, m. p. 113C-115C.
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2571-52-0.
Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2003/82787; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts