Ipso-nitration of aryl boronic acidsIpso-nitration of aryl boronic acids
SyntheticPage 722
Published Mar 06, 2014
The mixture of phenyl boronic acid (50 mg, 1 mmol) and bismuth (III) nitrate (397 mg, 2 mmol) in toluene (2 mL) was refluxed for 1.5 h. Reaction mixture was allowed to cool to room temperature and was filtered through filter paper. Residue was washed with ethyl acetate followed by dichloromethane. The combined organic layer was evaporated on rotary evaporator. Purified by silica gel column chromatography (mesh 100-200) using EtOAc-hexane (5: 95) as mobile phase gave nitrobenzene as yellowish liquid (45.5 mg, 90% yield). The product was characterized by comparison of NMR data with literature values (Manna, S.; Maity, S.; Rana, S.; Agasti, S.; Maiti, D. Org. Lett. 2012, 14, 1736-1739. http://dx.doi.org/10.1021/ol300325t)