Benzoyl Peroxide → 7-Bromomethylnaphthalene-1-carboxylic acid

Participants

Reaction Steps

A suspension of N-bromosuccinimide (6.23 g, 0.035 mol) in a solution of 7-methylnaphthalene-1-carboxylic acid (6.2 g, 0.033 mol) in tetrachlomethane (200 mL) was refluxed in the presence trace amounts of benzoyl peroxide for 2 hours. The resulting white suspension was evaporated to dryness under reduced pressure, washed with hot water and dried to give the crude product (8.46 g, 95.8%). An analytical sample was recrystallized from benzene-ethanol mixture. M.p. 209.5-211° C. 1H NMR δ 13.20 (bs, 1H), 8.91 (bs, 1H), 8.30-7.95 (m, 3H), 7.72-7.54 (m, 2H), 4.92 (s, 2H). Anal. Calcd for C12H9BrO2: C, 54.37; H, 3.42. Found: C, 54.45; H, 3.44.

Provenance & Evidence