Related Products of 25245-27-6,Some common heterocyclic compound, 25245-27-6, name is 1-Iodo-3,5-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.
In a dry two necked flask were introduced N-[2-(1-Phenyl-cyclohexa-2,5-dienyl)-ethyl]-methanesulfonamide 3c (169 mg, 0.610 mmol), silver carbonate (336 mg, 1.22mmol), triphenylphosphine (24 mg, 0.092 mmol), 3,5-dimethoxy-iodobenzene 4b (322 mg, 1.22mmol), palladium acetate (6.8 mg, 0.030 mmol) and acetonitrile (24.5 mL). The mixture waswarmed to 85C and stirred for 16 hours. The mixture was filtered through celite, which wasthen washed with ethyl acetate. Evaporation of the solvents led to a paste, which was purifiedthrough silica gel chromatography (Petroleum ether/EtOAc 70:30), affording 5c as a white solid(98 mg, 39%). Mp = 123-125 C. IR (solid, KBr, numax, cm-1): 3295, 2936, 2255, 1606, 1454,1316, 1203, 1149, 1064, 973, 910, 777, 735, 710. 1H NMR (300 MHz, CDCl3): deltaH 1.53-1.63(1H, m, CHaHxCH2N), 1.90 (1H, d, 3JHH 6.0 Hz, CH cyclopropane), 1.93-2.00 (1H, m,CHaHxCH2N), 2.36 (1H, dta, JHH 6.0, 2.5 and 2.5 Hz, CH cyclopropane), 2.82 (3H, s,NSO2CH3), 3.00-3.10 (2H, m, CH2N), 3.19-3.23 (1H, m, CH cyclopropane), 3.78 (6H, s, OCH3 x2), 4.43 (1H, broad s, NH), 5.16 (1H, ddd, JHH 5.3, 2.2 and 1.5 Hz, CH olefinic), 5.91 (1H, dta, J= 5.3, 2.0 and 2.0 Hz, CH olefinic), 6.33 (1H, t, 4JHH 2.3 Hz, CH aromatic), 6.36 (1H, t, 4JHH 2.3Hz, CH x 2 aromatic), 7.17-7.35 (5H, m, 5CH aromatic). 13C NMR (75.5 MHz, CDCl3): 36.9(CH cyclopropane), 37.7 (C aliphatic), 37.9 (CH cyclopropane), 40.0 (NSO2CH3), (CH2N), 41.7(CH2CH2N), 51.3 (CH allylic), 55.4 (OCH3 x 2), 98.5 (CH aromatic), 105.8 (CH x 2 aromatic),126.6 (CH aromatic), 128.2 (CH x 2 aromatic), 131.6 (CH olefinic), 131.7 (CH x 2 aromatic),134.1 (CH olefinic), 137.5, 146.6 (2C aromatic), 160.9 (C x 2 aromatic). MS(SIMS) m/z (%):436 (M+Na, 35), 414 (M+H, 100), 305 (35). HRMS calcd for (M+H) C23H28NO4S 413.1661;found 413.1655 (1.5 ppm).
The synthetic route of 25245-27-6 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Lebeuf, Raphael; Robert, Frederic; Landais, Yannick; ARKIVOC; vol. 2014; 3; (2013); p. 6 – 17;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com