4-Phenoxyphthalonitrile

31643-49-9

108-95-2

38791-62-7

General procedure for the synthesis of 4-phenoxyphthalonitrile from 4-nitrophthalonitrile and phenol: To a solution of tetrahydrofuran (THF, 15 mL) containing sodium hydride (NaH, 0.15 g) and phenol (0.353 g, 0.0375 mol), slowly add 4-nitrophthalonitrile (0.50 g, 0.0028 mol) to the THF (15 mL ) solution. The reaction mixture was heated to reflux for 8 hours. Upon completion of the reaction, 1,2-diisocyano-4-phenoxybenzene (8) was obtained by filtration and the solid was washed with ethyl acetate. The filtrate and washings were combined and the solvent was removed by evaporation under reduced pressure. The white precipitate obtained was purified by fast column chromatography using ethyl acetate: hexane (1:4) as eluent. The yield was 0.737 g in 86.4% with an Rf value of 0.36 (ethyl acetate: hexane, 1:4).1H NMR (300 MHz, CDCl3) δ 0.90 (s, 2H), 3.46 (m, 5H, CH), 7.07 (m, 3H, ArH).13C NMR (300 MHz, CDCl3) δ 71.01, 117.45, 119.69, 119.92, 126.95, 127.34, 134.43, 135.20.