Synthetic Route of 5460-32-2,Some common heterocyclic compound, 5460-32-2, name is 4-Iodo-1,2-dimethoxybenzene, molecular formula is C8H9IO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To a stirred solution of 1-iodo-3,4-dimethoxybenzene 8 (0.132g, 0.5mmol) in DMF (2.0mL) were added acrolein diethyl acetal (0.229mL, 1.5mmol), nBu4NOAc (0.302g, 1.0mmol), K2CO3 (0.104g, 0.75mmol), and Pd(OAc)2 (0.003g, 0.015mmol) and the mixture was stand for 4hat 90°C. After that period, the mixture was cooled, hydrochloric acid 2N was slowly added and the reaction was stirred at room temperature for 10min. Then, the mixture was diluted with ethyl ether (50mL) and washed with water (3×50mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with dichloromethane as eluent to give the desired (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde 9 in good yield (77mg, 80percent). 4.9.1 (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde (9) (0045) M.p. 80?82°C. 1H NMR (300MHz, CDCl3): delta 3.93 (s, 3H, 3-OCH3), 3.94 (s, 3H, 4-OCH3), 6.62 (dd, 1H, H-alpha, J 15.8, 7.8Hz), 6.91 (d, 1H, H-5, J 8.3Hz), 7.08 (d, 1H, H-2, J 2.0Hz), 7.17 (dd, 1H, H-6, J 8.3, 2.0Hz), 7.42 (d, 1H, H-beta, J 15.8Hz), 9.66 (d, 1H, CHO, J 7.8Hz) ppm. 13C NMR (75MHz, CDCl3): delta 55.8 and 55.9 (3,4-OCH3), 109.7 (C-2), 111.0 (C-5), 123.3 (C-6), 126.6 (C-alpha), 126.9 (C-1), 149.3 (C-3), 151.9 (C-4), 152.8 (C-beta), 193.5 (CHO) ppm. MS m/z (ESI+, percent): 193 ([M+H]+, 95), 215 ([M+Na]+, 100). HRMS (ESI+) m/z calcd. for C11H13O3 [M+H]+ 193.0859; found 193.0855.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodo-1,2-dimethoxybenzene, its application will become more common.
Reference:
Article; Proenca, Carina; Albuquerque, Helio M.T.; Ribeiro, Daniela; Freitas, Marisa; Santos, Clementina M.M.; Silva, Artur M.S.; Fernandes, Eduarda; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 381 – 392;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com