Anhydrous potassium carbonate (24.15 g, 175.01 mmol, 1.5 eq.) was added batchwise to a N,N-dimethylformamide (DMF, 100 mL) solution of 4-chlorophenol (15 g, 116.67 mmol, 1 eq.) at room temperature. After stirring for 2 min, methyl 2-bromoacetate (13.3 mL, 140.01 mmol, 1.2 equiv) was added dropwise to the reaction system. Subsequently, the reaction mixture was heated to 80 °C and kept for 4 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, the unfolding agent was a hexane solution of 5% ethyl acetate), and after confirming the complete consumption of the raw materials, the reaction mixture was cooled to room temperature. The reaction solution was diluted with deionized water (100 mL) and extracted with ethyl acetate (2 x 100 mL). The organic phases were combined, washed with saturated saline (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by fast column chromatography (Combiflash, silica gel column), and the eluent was a hexane solution of 15% ethyl acetate. The eluate containing the target compound was collected and concentrated under reduced pressure to give methyl 2-(4-chlorophenoxy)acetate (22.5 g, 96.5% yield) as a light yellow liquid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.67 (s, 3H), 4.78 (s, 2H), 6.91-6.95 (m, 2H), 7.28-7.32 (m, 2H).
