Electric Literature of 182056-39-9, A common heterocyclic compound, 182056-39-9, name is 2-Bromo-4-iodo-1-methoxybenzene, molecular formula is C7H6BrIO, 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.
At -100 C., 1 mmol of nBuLi (1 eq.) is added to a solution containing 1 mmol of 2-bromo-4-iodo-1-methoxy-benzene dissolved in 15 mL of distilled hexane. After 45 minutes of stirring at this temperature, 0.5 mmol of 3,4,5-trimethoxyacetophenone diluted in 5 ml of distilled toluene is added. This mixture is stirred for hours while letting the temperature rise up gradually and is then slowly hydrolyzed by a saturated NH4Cl solution up to a pH=7-8. After extraction with diethylether (3×20 mL), the collected organic phases are dried on Na2SO4 and concentrated in the rotary evaporator. The raw reaction product is taken up in 10 mL of CH2Cl2 to which a few grains of hydrated APTS is added, and then stirred for 3 hours at room temperature. The solution is washed with a saturated NaCl solution, extracted with CH2Cl24. After drying on Na2SO4 and concentration in the rotary evaporator, an oil is collected which is purified on silica gel. Yield 53%.H1 NMR: delta ppm, CDCl3 300 MHz: 3.65 (s, 3H), 3.78 (s, 6H), 3.85 (s, 3H), 5.30 (s, 1H), 5.70 (s, 1H), 6.50 (s, 2H), 6.80 (d, 1H, J=8.7 Hz), 7.36-7.46 (m, 2H). Mass spectroscopy (ESI) [M+Na]+=403. Elemental analysis: (MM=378.05) Calculated C, 57.01; H, 5.05. Found C, 56.78; H, 4.90.
The synthetic route of 182056-39-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS); US2010/129471; (2010); A1;,
Iodide – Wikipedia,
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