Synthesis
To a solution of N,N-dimethylformamide (DMF, 10 mL) of 4-nitrophenol (2.78 g, 20 mmol) and 2-bromoethyl methyl ether (3.6 g, 26 mmol) was added anhydrous potassium carbonate (K2CO3, 5.52 g, 40 mmol). The reaction mixture was stirred at 80 °C for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was subsequently quenched with deionized water (30 mL) and ethyl acetate (EtOAc, 40 mL). The organic and aqueous layers were separated and the aqueous layer was further extracted with ethyl acetate (2 x 25 mL). All organic extracts were combined, washed with saturated sodium chloride solution (brine, 2×20 mL), dried over anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to afford the target product, 4-nitrophenyl-2-methoxyethyl ether (3.9 g, 100% yield) as a yellow solid.
References
[1] Patent: WO2014/130693, 2014, A1. Location in patent: Paragraph 00544; 00546
[2] Patent: WO2015/6754, 2015, A2. Location in patent: Paragraph 00243; 00244
[3] European Journal of Medicinal Chemistry, 1980, vol. 15, # 5, p. 399 - 404
[4] Patent: US2005/277668, 2005, A1. Location in patent: Page/Page column 17
