[Synthesis]
Ethyl iodide (1.79 g, 11.5 mmol) was added to an N,N-dimethylformamide (DMF, 10 mL) mixture of 2-bromo-5-nitrophenol (1.0 g, 4.59 mmol) and potassium carbonate (1.59 g, 11.5 mmol). The reaction mixture was stirred at 70 °C for 4 h and subsequently cooled to room temperature. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (EtOAc, 2 x 75 mL). The organic phases were combined, washed sequentially with water and saturated saline, dried over anhydrous sodium sulfate and concentrated to afford the target product 2-bromo-5-nitrophenylethyl ether (1.10 g, 4.18 mmol, 91% yield). Mass spectrum (ESI) m/z: 248.0 ([M + H]+). 1H NMR (300 MHz, DMSO-d6) δ (ppm): 7.90 (d, J = 8.6 Hz, 1H), 7.81 (d, J = 2.5 Hz, 1H), 7.78-7.73 (m, 1H), 4.27 (q, J = 7.0 Hz, 2H), 1.40 (t, J = 7.0 Hz, 3H). |