Application of 555-21-5,Some common heterocyclic compound, 555-21-5, name is 4-Nitrophenylacetonitrile, molecular formula is C8H6N2O2, 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.
General procedure: To a screw top vial (5 mL) under N2 containing freshly distilled toluene (0.6 mL) were successively added an aromatic nitro compound (0.60 mmol), InI3 (14.9 mg, 0.030 mmol), and TMDS (318 muL, 1.80 mmol). After the vial was sealed with a cap that contained a PTFE septum, the mixture was stirred at 60 C (bath temperature), and monitored via TLC analysis. Sat. aq NaHCO3 solution (5 mL) was added to the resultant mixture, which was then extracted with EtOAc (3 × 6 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (n-hexane-EtOAc, 9:1 to 4:1) to afford the corresponding aniline derivative.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Nitrophenylacetonitrile, its application will become more common.
Reference:
Article; Sakai, Norio; Asama, Shun; Konakahara, Takeo; Ogiwara, Yohei; Synthesis; vol. 47; 20; (2015); p. 3179 – 3185;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts