Synthetic Route of 658-99-1, 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. 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
Preparation 10 4-Cyano-4-(3,4-difluorophenyl)-5-(1,3-dioxolan-2-yl)pentanoic acid A solution of 3,4-difluorobenzyl cyanide (20g, 0.13mol) in tetrahydrofuran (20ml) was added dropwise to a solution of lithium bis(trimethylsilyl)amide (1.0M, 144ml, 0,14mol) in tetrahydrofuran at 0C under nitrogen. The reaction mixture was allowed to warm to room temperature and stirred for 2 hours, after which time it was cooled to 0C and a solution of 2-bromomethyl-1,3-dioxolane (15ml, 0.14mol) in tetrahydrofuran (15ml) was added followed by tetra-n-butylammonium iodide (2g, 5.4mmol). The reaction mixture was warmed to room temperature and stirred for 18 hours. A further portion of solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1M, 144ml, 0.14mol) was added dropwise to the reaction mixture at 0C and then the mixture was allowed to warm to room temperature over 5 hours. The reaction mixture was cooled to 0C and a solution of ethyl 3-bromopropionate (18ml, 0.14mol) in tetrahydrofuran (20ml) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 18 hours. A solution of sodium hydroxide (7.8g, 0.20mol) in water (50ml) was added to the crude reaction mixture at 0C and the mixture then allowed to warm to room temperature. The reaction mixture was stirred for 36 hours. The reaction mixture was partitioned between water and diethyl ether, the organic layer re-extracted with water and the combined aqueous layers were acidified to pH 1.0 with aqueous hydrochloric acid (2N). The aqueous layer was extracted with ethyl acetate (x2), dried over Na2SO4and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluding with a gradient system of dichloromethane gradually changing to dichloromethane: methanol: acetic acid (95: 5: 1, by volume) to afford the title compound as a brown oil (15.0g, 37%) which solidified on standing. 1H-NMR (CDCl3): delta = 7.30 (1H, m), 7.20 (2H, m), 4.80 (1H, m), 3.95 (2H, m), 3.80 (2H, m), 2.50 (2H, m), 2.30 (2H, m), 2.20 (2H, m). m/z: 312 (MH+).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-(3,4-Difluorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; PFIZER INC.; Pfizer Limited; EP992493; (2000); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts