These common heterocyclic compound, 453566-15-9, name is Methyl 3-bromo-5-cyanobenzoate, 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. category: nitriles-buliding-blocks
To methyl 3-bromo-5-carbamoyl-benzoate (2.8 g, 10.8 mmol, 1.0 eq) was added POCI3 (30 mL) and the reaction heated at 100 C overnight. The POCI3 was removed under reduced pressure, water was added and the aqueous layer extracted with EtOAc. The combined organic extracts were dried (Na2SC>4), filtered and evaporated in vacuo to afford a crude residue which was purified by column chromatography (petroleum ethenEtOAc, 20:1 ) to give methyl 3-bromo-5-cyano-benzoate (2.5 g, 96 %). This material was dissolved in THF (30 mL) and LiOH.H20 (1.7 g, 41.6 mmol, 1.54 eq) and H20 (10 mL) were added. The mixture was stirred at room temperature overnight. The THF was removed under reduced pressure and the aqueous phase acidified with diluted HC1 and extracted with EtOAc. The combined organic extracts were dried (Na2SC>4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (CH2C12: MeOH, 50: 1) to give the title compound as a white solid (2 g, 85 %).LC-MS: m z 248.0, 249.9 [M+Na1H NMR (400 MHZ, DMSO) delta 13.67 (br s, 1H), 8.40 (s, 1H), 8.24 (s, 1H), 8.24 (s, 1H).
The synthetic route of Methyl 3-bromo-5-cyanobenzoate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; FOVEA PHARMACEUTICALS; FEUTRILL, John; LERICHE, Caroline; MIDDLEMISS, David; WO2013/37705; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts