N-bromobutanimide → 8-Bromo-2-naphthol

Participants

Reaction Steps

In two side by side reactions, 8-bromo-2-tetralone (7.0 g, 31.25 mmol) and N-bromosuccinimide (5.84 g, 32.8 mmol) were combined in carbon tetrachloride and refluxed 45 min. The reactions were cooled, filtered through diatomaceous earth (Celite™), and combined for workup. The organic solution was washed with saturated aqueous sodium bicarbonate and brine followed by drying through phase separating filter paper (1 PS) and concentrated to give 14.44 g (104% crude) of 8-bromo-2-naphthol as a brown solid which was suitable for further reaction. A sample dissolved in methylene chloride and treated with activated carbon, concentrated, and triturated with hexane had: mp 96-100° C.; 1HNMR (250 MHz, CDCl3) δ 7.79-7.73 (m, 3 H), 7.56 (d, J=4.5 Hz, 1 H), 7.22-7.14 (m, 3 H). HRMS m/e calculated for C10H7BrO: 221.9680. Observed m/e: 221.9664.

Provenance & Evidence