p-Toluenesulfonic acid → Ethyl 1-(3-bromophenyl)cyclopropanecarboxylate

Participants

Reaction Steps

1-(3-Bromophenyl)cyclopropanecarboxylic acid (976 mg, 4.05 mmol) was dissolved in ethanol (20 mL) and p-toluenesulfonic acid (139 mg, 0.810 mmol) was added. The reaction mixture was heated at reflux for 15 h. The temperature of the oil bath was increased from 80° C. to 110° C. and the reaction mixture was stirred for 2 h at that temperature, after which the mixture was cooled and the solvent was removed under reduced pressure. The crude material was purified via flash chromatography (pentane:ethyl acetate 9:1) to afford ethyl 1-(3-bromophenyl)cyclopropanecarboxylate as a colorless oil (950 mg, 87.2%). 1H NMR (400 MHz, CDCl3) δ 1.13-1.20 (m, 5H), 1.57-1.62 (m, 2H), 4.10 (q, 2H), 7.17 (s, 1H), 7.27 (s, 1H), 7.38 (s, 1H), 7.47-7.50 (m, 1H).

Provenance & Evidence