Ethyl Acetate → 1-Naphthalenecarboxylic acid, 4-(bromomethyl)-, methyl ester

Participants

Reaction Steps

To a stirred solution of 4-methyl-naphthalene-1-carboxylic acid methyl ester (Preparation 50, 10.85 g, 54.18 mmol) in CCl4 (500 mL) was added N-bromosuccinamide (9.93 gm, 55.81 mmol) followed by AIBN (0.1 g, 0.612 mmol) at room temperature. Resulting reaction mixture was refluxed for 3 hours. Progress of reaction was monitored by TLC using 5% EtOAc in hexane. Rf of new spot and starting material was 0.8 and 0.7 respectively. After consumption of starting material, reaction mixture was concentrated in vacuo to residue. Residue was dissolved in EtOAc (300 mL) and washed with water (2×300 mL), brine (300 mL), dried over sodium sulphate and evaporated in vacuo to get pale yellow semisolid. Crude was purified by column chromatography using 100-200 mesh silica gel. Desired product was eluted in 4% EtOAc in hexane to afford white solid (10.5 g, 69.39%). 1H NMR (400 MHz, CDCl3) δ: 4.00 (s, 3H), 4.93 (s, 2H), 7.56 (d, J=7.48 Hz, 1H), 7.62-7.68 (m, 2H), 8.06 (d, J=7.4 Hz, 1H), 8.17-8.20 (m, 1H), 8.90-8.93 (m, 1H).

Provenance & Evidence