5460-32-2, name is 4-Iodo-1,2-dimethoxybenzene, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 5460-32-2
To a solution of the appropriate 4-iodobenzene 7a,b (1.0 mmol)in DMF (10 mL) were added the following reagents through thereferred order: acrolein diethyl acetal (0.46 mL, 3.0 mmol), nBu4-NOAc (0.603 g, 2.0 mmol), K2CO3 (0.207 g, 1.5 mmol), and Pd(OAc)2 (6.7 mg, 0.03 mmol) (for 8a) or PdCl2 (5.3 mg, 0.03 mmol) (for 8b). This mixturewas stirred at 90 ¡ãC for 4 h for 8a and 21 h for 8b. After this period, it was poured onto ice (50 g) and H2O (100 mL) and thepH was adjusted to 1 with diluted HCl. In the case of 8a, this aqueous solution was extracted with Et2O (3 50 mL) and theorganic layer was dried over anhydrous Na2SO4. In the case of 8b, the obtained precipitate was filtered off, taken in CH2Cl2 and driedover anhydrous Na2SO4. The solvent was evaporated to the dryness and both residues were purified by silica gel column chromatographyusing CH2Cl2 as eluent.4.1.7.1. (E)-3,4-Dimethoxycinnamaldehyde (8a). White solid(102 mg, 53percent yield); Rf 0.28. Mp 80-82 ¡ãC. 1H NMR (300.13 MHz,CDCl3): delta 9.66 (d, J 7.8 Hz, 1H, CHO), 7.42 (d, J 15.8 Hz, 1H, H-b), 7.17(dd, J 8.3 and 2.0 Hz, 1H, H-6), 7.08 (d, J 2.0 Hz, 1H, H-2), 6.91 (d, J8.3 Hz, 1H, H-5), 6.62 (dd, J 15.8 and 7.8 Hz, 1H, H-a), 3.94 (s, 3H, 4-OCH3), 3.93 (s, 3H, 3-OCH3) ppm. 13C NMR (75.47 MHz, CDCl3):delta 193.5 (CHO), 152.8 (C-b), 151.9 (C-4), 149.3 (C-3), 126.9 (C-1), 126.6(C-a), 123.3 (C-6), 111.0 (C-5), 109.7 (C-2), 55.9 and 55.8 (3,4-OCH3)ppm. ESI-MS m/z (percent): 215 ([M+Na]+, 100), 193 ([M+H]+, 95). ESIHRMSm/z calcd for [C11H12O3H]: 193.0865, found: 193.0855.
The synthetic route of 5460-32-2 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Sousa, Joana L.C.; Proenca, Carina; Freitas, Marisa; Fernandes, Eduarda; Silva, Artur M.S.; European Journal of Medicinal Chemistry; vol. 119; (2016); p. 250 – 259;,
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