[Synthesis]
General procedure: With reference to the method reported by An et al [1], 2-chloro-1,3-benzenediol (1.0 eq.) was dissolved in acetone (0.1 M), potassium carbonate (5.0 eq.) was added and stirred for 10 min. Subsequently, iodomethane (2.6 eq.) was added and the reaction mixture was stirred under reflux conditions for 16 hours. After completion of the reaction, it was cooled to room temperature, water was added and extracted three times with ether. The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the target product 2-chloro-1,3-dimethoxybenzene (4c).
2-Chloro-1,3-dimethoxybenzene (4c): light yellow solid (76 mg, 0.44 mmol, 88% yield). Thin layer chromatography (TLC) (unfolding agent: hexane/ethyl acetate=10:1) Rf value was 0.38; infrared spectra (ATR) νmax: 3011 (w), 2966 (w), 2947 (w), 2840 (w), 1594 (m), 1472 (m), 1435 (m), 1299 (m), 1253 (m), 1191 (w). 1174 (w), 1099 (m), 1053 (m), 1025 (m), 849 (w), 764 (m), 709 (m), 654 (m), 597 (m) cm-1; UV-Vis spectra λmax (logε): 280 (3.08), 274 (3.10), 230 (3.79) nm. |