Nitric Acid → (2-Nitrophenyl)boronic acid

Participants

Reaction Steps

A solution of phenylboronic acid (10 g; 82 mmol) in acetic acid anhydride (100 ml) at −15° C. was added fuming HNO3 (5 ml; 120 mmol) over 30 min such that reaction temperature was kept below −10° C. The reaction mixture was allowed to warm up to rt. and left with stirring over night. The reaction mixture was poured onto ice and concentrated to 50 ml. The remanense was then re-evaporated 5 times from additional H2O (100 ml) and finally filtered to give 7.1 g crude product as a mixture of isomers. Column chromatography (CH2Cl2/EtOH=10/0.5) gave 4.8 g (35%) pure product as an oil.

Provenance & Evidence