Nitric Acid → (2-Nitrophenyl)boronic acid

Participants

Reaction Steps

A solution of phenyl boronic acid (5.0 g, 41 mmol) in acetic anhydride (50 mL) at −15° C. was treated with nitric acid (2.5 mL) dropwise over 30 minutes maintaining a temperature below −10° C. The reaction was allowed to warm to room temperature overnight, then poured onto ice. The resulting solution was concentrated to 25 mL and water (50 mL) was added. The mixture was again concentrated. This procedure was repeated five times. The solid that developed was filtered and dried. The crude product was purified by flash chromatography (SiO2, 2% EtOH/CH2Cl2) to afford the desired product (1.0 g, 15%).

Provenance & Evidence