Ethyl Acetate → 5-Hydroxy-2-nitrobenzonitrile

Participants

Reaction Steps

To a 0° C. solution of 578 mg (2.28 mmol) 5-phenyl-methoxy-2-nitrobenzonitrile, prepared according to the procedure of E. Elslager, et. al., J. Heterocyclic Chem. 1972, 9, 759-773, in 5 mL of dichloromethane at 0° C. was added 2.6 mL (2.62 mmol, 1.15 equiv) of a 1.0 M solution of boron tribromide in dichloromethane. After the reaction mixture was stirred for 3 h, it was diluted with ethyl acetate, washed sequentially with 1N aqueous sodium hydrogen sulfate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated to give 357 mg (96%) of the title compound which was used without further purification: 1H NMR (400 MHz, CD3OD) δ8.17 (d, 1H, J=9.2 Hz), 7.03 (d, 1H, J=2.7 Hz), 6.92 (dd, 1H, J=2.7, 9.3 Hz).

Provenance & Evidence