Category: 5471-81-8

Adding a certain compound to certain chemical reactions, such as: 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5471-81-8, name: Methyl 4-iodo-3-methylbenzoate

General procedure: In Scheme VIII, the bromobenzyldiazepan XXXIV is coupled with a substituted iodobenzoate ester XXXVIII (from Scheme VII) in the presence of diboron pinacol ester (B2pin2) to form the biphenyl ester XLI with substitution in both phenyl rings.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-iodo-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; ZECH, Stephan, G.; KOHLMANN, Anna; LI, Feng; WANG, Yihan; ZHOU, Tianjun; DALGARNO, David, C.; SHAKESPEARE, William, C.; ZHU, Xiaotian; WO2014/151761; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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

5471-81-8, Adding a certain compound to certain chemical reactions, such as: 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5471-81-8.

Specific operation: In a 25 mL reaction flask equipped with a magnetic stirrer, a metal catalyst palladium acetate (6.7 mg, 0.03 mmol), triphenylphosphine (20.0 mg, 0.075 mmol) was added, S-2-bromophenyl-S-methyliminosulfanone (70.0 mg, 0.3 mmol), norbornene (56.4 mg, 0.6 mmol), potassium carbonate (82.8 mg, 0.6 mmol),Nitrogen protection (at least three nitrogen cycles), followed by a mixture of acetonitrile and N,N-dimethylformamide in a nitrogen stream (V/V=1, 3 ml)And methyl 4-iodo-3-methylbenzoate (99.4 mg, 0.36 mmol), closed vessel.The reaction solution was heated to 80 C. for about 12 h, and the reaction was complete by TLC.In the post-treatment, the reaction solution is first diluted with 15 ml of ethyl acetate, and then filtered through a sand funnel filled with silica gel.Remove inorganic substances such as catalysts and alkalis,The resulting filtrate was separated by flash column chromatography to give the pure product 5,7-dimethyldibenzo[c,e][1,2]thiazine-9-carboxylic acid methyl ester-5-oxide compound 3m. Yield: 87%.

According to the analysis of related databases, 5471-81-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangxi Normal University; Chen Zhiyuan; Zhou Hao; Wang Xiumei; (17 pag.)CN107987034; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5471-81-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 5471-81-8 as follows.

Under a protective atmosphere of inert gas, Pd(OAc)2 (2.2 mg, 10 mol%), XPhos (19.1 mg, 20 mol%), NBE-CO2K (3.5 mg, were added to a 4.0 mL reaction flask equipped with a magnetic stir bar. 10 mol%), 3-methyl-4 iodine benzoate Methyl ester (0.2 mmol, 1.0 equiv.), 1,2-epoxyoctadecane (0.6 mmol, 3.0 equiv.) and dry N-methylpyrrolidone (1.0 mL). The reaction flask was capped and stirred at room temperature for about 5 minutes, after which the mixture was heated to 80 C and stirred 24hour. After the reaction vessel was cooled to room temperature, it was quenched with water (10 mL), extracted with methyl tert-butyl ether (3¡Á10 mL), dried Na2SO4 Dry, filter, and concentrate under vacuum. Purified by column chromatography, the eluent was petroleum ether: ethyl acetate = 50:1 (v/v),67 mg of methyl 7-methyl-2-n-hexadecyl-2,3-dihydrobenzofuran-5-carboxylate (white solid, yield 80%).

According to the analysis of related databases, Methyl 4-iodo-3-methylbenzoate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wuhan University; Zhou Qianghui; Wu Chenggui; Cheng Honggang; (20 pag.)CN108329285; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5471-81-8,Some common heterocyclic compound, 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, molecular formula is C9H9IO2, 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.

Under a protective atmosphere of inert gas, Pd(OAc)2 (2.2 mg, 10 mol%), XPhos (19.1 mg, 20 mol%), NBE-CO2K (3.5 mg, were added to a 4.0 mL reaction flask equipped with a magnetic stir bar. 10mol%),Methyl 3-methyl-4-iodobenzoate (0.2 mmol, 1.0 equiv.),Methyl glycidyl ether (0.6 mmol, 3.0 equiv.) and dry N-methylpyrrolidone (1.0 mL). The reaction flask was capped and stirred at room temperature for about 5 minutes, after which the mixture was heated to 80 C and stirred 24hour. After the reaction vessel was cooled to room temperature, it was quenched with water (10 mL), extracted with methyl tert-butyl ether (3¡Á10 mL), dried Na2SO4Dry, filter, and concentrate under vacuum. Purified by column chromatography,The eluent is petroleum ether: ethyl acetate = 10:1 (v/v),34 mg of methyl 7-methyl-2-(methoxymethyl)-2,3-dihydrobenzofuran-5-carboxylate (light yellow oily liquid, yield 72%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-iodo-3-methylbenzoate, its application will become more common.

Reference:
Patent; Wuhan University; Zhou Qianghui; Wu Chenggui; Cheng Honggang; (20 pag.)CN108329285; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5471-81-8, A common compound: 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

(c) Preparation of methyl 3-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate Following the basic procedure of Example 7(f), by reacting 2.8 g (10 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acid with 1.84 g (6.7 mmol) of methyl 3-methyl-4-iodobenzoate, 1.37 g (53%) of methyl 3-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate was obtained in the form of a yellow oil.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-iodo-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; C.I.R.D. Galderma; US5723499; (1998); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5471-81-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 5471-81-8 as follows.

General procedure: To a 25mL of oven-dried Schlenk tube equipped with a magnetic stir bar was charged with [Pd(C3H5)Cl]2 (3.7mg 0.01mmol, 0.05 equiv), XPhos (10.5mg, 0.022mmol, 0.11 equiv), K2CO3 (69.1mg, 0.5mmol, 2.5 equiv), and dry CH3CN (1mL). After stirring for about 15minat r.t. under argon, a solution of aryl iodide 1 (0.24mmol, 1.2 equiv), alkylating reagent 2 (0.2mmol, 1.0 equiv), 5-Norbornene-2-carboxylic acid N4 (5.5mg, 0.04mmol, 0.2 equiv) in dry MeCN (1mL) was added, then heated to 70C and stirred for 5-24h. The reaction was monitored by TLC, after completion of the reaction, the mixture was cooled to r.t., filtered through a thin pad of celite eluting with ethyl acetate (10mL), and the combined filtrate was concentrated in vacuo. The residue was directly purified by column chromatography on silica gel or purified by PTLC to give the desired product 3.

According to the analysis of related databases, Methyl 4-iodo-3-methylbenzoate, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Ze-Shui; Qian, Guangyin; Gao, Qianwen; Wang, Peng; Cheng, Hong-Gang; Hua, Yu; Zhou, Qianghui; Tetrahedron; vol. 75; 12; (2019); p. 1774 – 1780;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com