Nitric Acid → 6-Bromo-2-methoxy-1-nitronaphthalene

Participants

Reaction Steps

An ice-cooled solution of 100% nitric acid (12.0 ml, 0.27 mol) in 95 ml of acetic anhydride was added dropwise to a solution of 6-bromo-2-methoxynaphthalene (61.7 g, 0.26 mol) and 0.25 ml of conc. sulfuric acid in 570 ml of acetic anhydride while maintaining the temperature at +30° to +40° C. The mixture was stirred for an additional 10 min. and filtered. The solid was washed with water and dried to give 60.0 g (73%) of the nitro compound. M.p. 151°-152° C., 1H-NMR (CDCl3): 3.98 (s, 3H, CH3), 7.16-7.93 (m, 5H, ArH).

Provenance & Evidence