Hydrogen Bromide → 8-Bromonaphthalene-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

According to the procedure of W. Adcock, et al. Aust. J. Chem. 18, 1351 (1965) and H. H. Hodgson, et al. J. Chem. Soc., 1620 (1933), to a cooled (10° C.), stirred solution of NaNO2 (1.24 g, 0.0179 mol) in H2SO4 (16.1 mL) and HOAc (14.9 mL) [prepared by adding NaNO2 to cooled (10° C.) H2SO4, heating to dissolve, recooling, and adding HOAc] was added a solution of 8-amino-2-naphthoic acid (2.80 g, 0.0150 mol) in HOAc (50 mL) over 10 minutes. The resulting solution was added slowly (over 10 minutes) to a heated (60° C.), stirred solution of CuBr (9.44 g, 0.0658 mol) in concentrated HBr (90 mL). The mixture was warmed to 90° C. for 10 minutes, cooled, diluted with H2O (200 mL) and filtered to give a green solid, 3.4 g. The crude product was combined with similarly prepared material (450 mg) and recrystallized from EtOH to give an off-white solid (2.3 g, 55%), m.p. 265°-266° C.

Provenance & Evidence