The synthetic route of 5471-81-8 has been constantly updated, and we look forward to future research findings.
In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 5471-81-8
A 3 -Liter round bottom flask equipped with a mechanical stirrer, thermocouple, and addition funnel was charged with 100 g of solid 4-iodo-3-methylbenzoic acid methyl ester and 1.0 L of dry THF. The mixture was cooled to -25 0C, and 218 mL of i-PrMgCl (2M in THF) was added dropwise over 25 min while the internal temperature was maintained at <-15 0C. The batch was kept at <-10 0C for 1 hr after the addition of the Grignard reagent. Analysis of a hydrolyzed aliquot showed greater than 97% deiodination. The reaction was then cooled to about -20 0C and quenched with trimethyl borate (77 g). The trimethyl’ borate reaction is exothermic. The temperature increased to about -4 0C during the addition of the trimethyl borate over a time of about 3 min. The resulting solution was aged for 1 h at <0 0C. The batch was then cooled to about -20 0C and further quenched with 1.0 L of IM H3PO4. This quench was also exothermic, raising the temperature to 3 0C by the end of the quench. The batch was aged at room temperature overnight.The THF was then removed by distillation at < 45 0C under reduced pressure. The product slurry was allowed to cool to room temperature, and then was filtered. The cake was washed with water (3 X 500 ml) and toluene (2 X 250 mL) and then was dried under vacuum with nitrogen sweep for 18 h to give the boronic acid 3 as an off-white crystalline solid.
The synthetic route of 5471-81-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MERCK & CO., INC.; WO2007/79186; (2007); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com