Hydrogen Bromide → Methyl 3-bromo-4-cyanobenzoate

Participants

Reaction Conditions

Reaction Steps

Add 3-amino-4-cyano-benzoic acid methyl ester (1.1 g, 6.24 mmol) to a stirred solution of sodium nitrite (511 mg, 7.4 mmol) in concentrated sulfuric acid (5 ml) and glacial acetic acid (5 ml) at 40° C. After 30 min at 40° C., pour the resulting orange solution into a cold solution of copper bromide (1.42 g, 9.89 mmol) in 48% hydrobromic acid (5 ml). When the evolution of nitrogen is finished, heat the mixture to 90° C. for 30 min. Cool down to room temperature and pour the mixture onto crushed ice. Filter out the resulting dark solid, wash with water. Take this solid up in chloroform and filter the inorganic solid. Concentrate the filtrate to yield a crude yellow residue. Purification by flash chromatography (Silica gel-hexane/EtOAc) yields the title compound (56%).

Provenance & Evidence