Hydrochloric Acid → 4-Nitrobenzoylacetonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-4′-nitroacetophenone (30 g, 0.123 mol) in ethanol (200 mL) at 0° C. was added a solution of NaCN (18 g, 0.368 mol) in H2O (60 mL) dropwise over 1 h. Upon completion of the addition, the mixture was stirred at 0° C. for an additional hour and then diluted with H2O (200 mL). The solution was treated with 1N aq. HCl solution, to a pH of 2, and extracted with CH2Cl2 (2×500 ML). The combined organic layers were dried over Na2SO4 and concentrated by rotary evaporation. The residue was purified by flash chromatography on silica gel eluting with 1:1 hexane/EtOAc to obtain 2-cyano-4′nitroacetophenone as an orange solid.

Provenance & Evidence