1,2-Dibromoethane → 2-(4-Amino-3-nitrophenoxy)ethyl bromide

Participants

Reaction Steps

A round-bottom flask was charged with 4-amino-3-nitrophenol (15.4 g, 0.1 mol, commercially available from Aldrich), acetone (600 mL), 1,2-dibromoethane (34.5 mL, 0.4 mol) and cesium carbonate (39 g, 0.12 mol). The mixture was refluxed 15 hours with stirring. The mixture was filtered to remove the salt, the filtrate was concentrated. Purification by the silica gel chromatography gave 4-(2-bromoethoxy)-2-nitroaniline (6.5 g). 1H-NMR (400 MHz, CDCl3): δ 7.57 (d, 1H), 7.12 (dd, 1H), 6.80 (d, 1H), 5.95 (s, br, 2H), 4.27 (t, 2H), 3.64 (t, 3H). MS (EI): 262 (MH+).

Provenance & Evidence