The review summarizes the existing methods for the synthesis of 3-nitrobenzofurans and their polycondensed derivatives which are valuable substrates for dearomatization of the furan ring. The main attention is paid to the electrophilic nitration of 3-unsubstituted benzofurans and the preparation of 5-amino- and 5-hydroxy-3-nitrobenzofurans via the Nenitzescu indole synthesis from quinones or quinone monoimines and β-nitroenamines.