1.00 g (6.37 mmol) of 2-fluoro-5-nitrophenol was dissolved in 15 ml of N,N-dimethylformamide (DMF) and 1.76 g (12.7 mmol) of potassium carbonate was added as a base. Subsequently, 1.19 g (7.64 mmol) of ethyl iodide was added as alkylation reagent and the reaction mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the reaction mixture was poured into a mixture of 100 ml of toluene and 100 ml of water to separate the organic and aqueous phases. The aqueous phase was extracted twice with 150 ml of toluene and the organic phase was combined. The organic phase was washed with saturated aqueous sodium bicarbonate to remove residual acid and then dried with anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting solid was dried under high vacuum to give 1.06 g (89% yield) of 2-ethoxy-1-fluoro-4-nitrobenzene. The product was characterized by 1H NMR (400 MHz, DMSO-d6) and GC/MS: 1H NMR (δ/ppm): 7.95 (dd, 1H), 7.89 (ddd, 1H), 7.52 (dd, 1H), 4.25 (q, 2H), 1.38 (t, 3H); GC/MS (EI-pos): m/z = 185 ( M + H)+, retention time (Rt) = 6.42 min.
