1-Naphthoic acid → 5-Bromonaphthalene-1-carboxylic acid

Participants

Reaction Steps

To a solution of 1-naphtoic acid (commercially available) (15 g) in acetic acid (37 ml) was added dropwise bromine (4.5 ml). The reaction mixture was heated at reflux for 4 hours. The reaction mixture was then cooled to ambient temperature and stored at ambient temperature for 16 hours. The solids were isolated by filtration and washed with acetic acid and then ethanol to give 5-bromo-1-naphtoic acid (10.8 g) as a white solid. 1H-NMR (DMSO, 400 MHz): 8.85 (d, 1H), 8.40 (d, 1H), 8.21 (d, 1H), 7.98 (d, 1H), 7.76 (m, 1H), 7.55 (m, 1H).

Provenance & Evidence