2-Iodo-1 3-dimethoxybenzene 97

151-10-0

16932-44-8

General procedure for the synthesis of 2-iodo-1,3-dimethoxybenzene from 1,3-dimethoxybenzene: To a solution of 1,3-dimethoxybenzene (25 g, 180 mmol) in ether (150 mL) was slowly added butyllithium (112.5 mL 1.6 M hexane solution, 180 mmol). The reaction mixture was stirred for 30 hours and then cooled to -35°C. Iodine (45.7 g, 180 mmol) was added and the reaction mixture was stirred at 20 °C for 24 h, then poured into 10% aqueous sodium bisulfite solution (60 mL). The aqueous phase was separated and extracted with ethyl acetate (2 x 60 mL). The organic extracts were combined, washed sequentially with saturated aqueous sodium thiosulfate (60 mL), brine (60 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. Purification of the product by crystallization (diethyl ether) afforded 2-iodo-1,3-dimethoxybenzene (34 g, 71%) as a white solid; melting point 105-106 °C (literature value 104 °C) [1]; 1H NMR (CDCl3): δ 3.80 (s, 6H), 6.43 (d, J=8.4 Hz, 2H), 7.17 (t, J=8.4 Hz, 1H) ; 13C NMR (CDCl3): δ 56.6, 76.3, 103.9, 129.8, 159.5; analytical calculated values for C8H9IO2: C, 36.39; H, 3.44; measured values: C, 36.40; H, 3.46.