Cesium carbonate → Ethyl 4-(3-bromophenoxy)butanoate

Participants

Reaction Steps

To a solution of 3-bromophenol (2 g, 11.56 mmol) in dimethylformamide (10 mL) was added sequentially cesium carbonate (11.30 g, 34.7 mmol) and ethyl 4-bromobutanoate (1.66 mL, 11.6 mmol) at room temperature. The heterogeneous reaction mixture was stirred at room temperature for 2.5 h. The reaction mixture was partitioned between ether (75 mL) and water (50 mL). The ether layer was collected, washed with brine (50 mL), dried over sodium sulfate, and concentrated to yield ethyl 4-(3-bromophenoxy)butanoate (3.3 g, 11.5 mmol, 99% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.25-1.29 (m, 3H), 2.07-2.15 (m, 2H), 2.48-2.54 (m, 2H), 3.99 (t, J=6.16 Hz, 2H), 4.13-4.15 (m, 1H), 4.16-4.19 (m, 1H), 6.80-6.84 (m, 1H), 7.05 (t, J=1.98 Hz, 1H), 7.06-7.09 (m, 1H), and 7.11-7.16 (m, 1H).

Provenance & Evidence