These common heterocyclic compound, 2974-94-9, name is 1-Iodo-4-phenoxybenzene, its 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. HPLC of Formula: C12H9IO
Example 9 1-(2-{[3-(4-Phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine Using the general method of Example 7, 1-[2-(2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.50 g, 1.88 mmol) was reacted with 4-iodophenyl phenyl ether (0.78 g, 2.63 mmol). The crude product was purified by column chromatography eluding with 95/5 dichloromethane/methanol to provide a solid. The solid was slurried with aqueous sodium hydroxide to remove salts and then purified by column chromatography eluding with 9/1 ethyl acetate/methanol to provide a solid. This material was further purified by column chromatography eluding with 99/1 ethyl acetate/methanol to provide 24 mg of 1-(2-{[3-(4-phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a solid, m.p. 146-148 C. Analysis. Calculated for C27H22N4O2.(H2O)4/5: %C, 72.24; %H, 5.30; %N, 12.48. Found: %C, 71.82; %H, 4.85; %N, 12.35. 1H NMR (300 MHz, DMSO-d6) delta 8.18 (s, 1H), 8.12 (d, J=7.4 Hz, 1H), 7.62 (d, J=7.7 Hz, 1H), 7.41-7.47 (m, 3H), 7.18-7.27 (m, 4H), 7.06 (dd, J=7.6, 1.0 Hz, 2H), 6.90 (dd, J=6.7 Hz, 2H), 6.71 (s, 2H), 4.85 (t, J=5.1 Hz, 2H), 4.37 (s, 2H), 4.02 (t, J5.0 Hz, 2H); IR (KBr) 3444, 3070, 2928, 1500, 1230, cm-1; HRMS (EI) Calculated for C27H22N4O2 (M+) 434.1743, found 434.1748.
The synthetic route of 1-Iodo-4-phenoxybenzene has been constantly updated, and we look forward to future research findings.
Reference:
Patent; 3M Innovative Properties Company; US6677348; (2004); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com