19472-74-3, A common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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.
Example 33A A round bottom flask was charged under inert atmosphere with copper iodide (760 mg, 4 mmol), cesium carbonate (3.91 g, 12 mmol) then dimethylformamide (20 mL), previously degassed, was added followed by 2-Bromophenylacetonitrile (519 muL, 4 mmol), 3-Methylpyrazole (3.32 mL, 40 mmol) and N-N’-dimethylethylenediamine (425.86 muL, 4 mmol). The reaction mixture was heated to 120 C. for 2.5 hours. After cooling the reaction mixture was filtered through a Celite pad that was rinsed with dimethylformamide. The volume was reduced under reduced pressure, saturated ammonium chloride aqueous solution was added and extracted with ethyl acetate. The organic phase was washed with saturated aqueous NH4Cl solution, brine then dried over Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography on SiO2 using cyclohexane/ethyl acetate mixture of increasing polarity (from 100% cyclohexane to 100% ethyl acetate) as eluant. The oil obtained was further purified by SPE cartridge Stratosphere ?PL-THIOL MP? to remove copper salts. 300 mg of the title compound (38%) were obtained.GC-MS (Method 3A.1): Rt: 10.47 minMS: 197 [M]+.
The synthetic route of 19472-74-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/115863; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts