Ethanol → 1-(4-Bromophenyl)cyclobutane-1-carboxylic acid

Participants

Reaction Steps

To a solution of 1-(4-bromophenyl)cyclobutanecarbonitrile (1.0 g, 4.2 mmol) in EtOH (28 mL) and water (2 mL) was added KOH (2.1 g, 42 mmol). The reaction mixture was heated to reflux for 16 hours. The reaction was then quenched with 1M hydrochloric acid in order to adjust pH to 7. The organic solvents were removed in vacuo to give a residue, which was dissolved in ethyl acetate (40 mL), then washed with brine (3×10 mL). The organic phase was concentrated in vacuo, and the resulting oil was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=8:1) to give 1-(4-bromophenyl)cyclobutanecarboxylic acid (0.8 g, 79% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.47 (d, 2 H), 7.19 (d, 2 H), 2.70-2.63 (m, 2 H), 2.33-2.26 (m, 2 H), 1.89-1.87 (m, 1 H), 1.75-1.71 (m, 1 H).

Provenance & Evidence