1-Fluoro-2-nitrobenzene → N-(4-methoxybenzyl)-2-nitroaniline

Participants

Reaction Steps

A mixture of 1-fluoro-2-nitrobenzene (20 g) and 4-methoxybenzylamine (18.52 ml) in dry tetrahydrofuran (100 ml) was stirred at 23° for 18 h under a nitrogen atmosphere. The mixture was filtered, then the organic layer was concentrated in vacuo to an oil. Ethanol (50 ml) was added and a solid separated. After filtration, the title compound was obtained as an orange solid (16.35 g). The filtrate was concentrated in vacuo and the residue was treated with further ethanol (10 ml) to give a further amount of title compound (7.9 g). M.p. 81°-2° T.l.c. CH-EA (8:2), Rf 0.55.

Provenance & Evidence