Category: 5471-81-8

Synthetic Route of 5471-81-8, These common heterocyclic compound, 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, 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.

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-epoxydodecane (0.6 mmol, 3.0 equiv.) and dry N-methylpyrrole Alkanone (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 (3×10 mL), dried Na2SO4 Dry, filter, and concentrate under vacuum. Purified by column chromatography, the eluent was petroleum ether: ethyl acetate = 50:1 (v/v) to give 7-A Methyl 4-n-decyl-2,3-dihydrobenzofuran-5-carboxylate 45 mg (yellow oily liquid, yield 67%)

The synthetic route of 5471-81-8 has been constantly updated, and we look forward to future research findings.

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

Application of 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.

A solution of methyl 4-iodo-3-methylbenzoate (21 .7 mmol, 6 g) in dry THF (120 mL) was purged with argon. The solution was cooled to -155C, /-PrMgCI (2M in THF, 108.5 mmol, 54.25 mL), and DMF (130.2 mmol, 10 mL) were added and the reaction was stirred for 2 h at -155C and then warmed to 255C and allowed to react for an additional hour. The reaction was quenched with aqueous 1 N HCI and extracted with EtAcO. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude was purified by flash chromatography on silica gel using an elution of 6% ethylacetate in hexanes to give methyl 4-formyl-3-methylbenzoate (3.08g .Yield: 80%). 1 H NMR (400 MHz, CDCI3) delta 10.35 (1 H, s), 8.00 (1 H, d, J=8Hz), 7.99 (1 H, s), 7.86 (1 H, d, J=8Hz), 3.95 (3H, s), 2.72 (3H, s) LC-MS: tR = 2.85 [M+H]+ = not ion (method 3).

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; ALMIRALL, S.A.; DRACONIS PHARMA, S.L.; LABORATORIOS DEL DR. ESTEVE, S.A.; AGUILAR, Nuria; FERNANDEZ, Joan, Carles; TERRICABRAS, Emma; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/149997; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 5471-81-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5471-81-8 name is Methyl 4-iodo-3-methylbenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

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.),(R)-Benzyl 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. Mix for 24 hours. The reaction vessel was cooled to rt then EtOAc (EtOAc)The Na2SO4 was dried, filtered and concentrated in vacuo. Purified by column chromatography, the eluent was petroleum ether: ethyl acetate = 10:1 (v/v),58 mg of methyl 7-methyl-2-(benzyloxymethyl)-2,3-dihydrobenzofuran-5-carboxylate (light yellow oily liquid, yield 93%, ee > 99%).

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

Reference of 5471-81-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

A solution of methyl 4-iodo-3-methylbenzoate (2.0 g, 7.2 mmol) in THF (30 mL) under ? was cooled to -20 C, a solution of /so-propylmagnesium chloride (2 M in THF, 4 mL, 8.0 mmol) was added dropwise and the suspension stirred at -20 C for 1 hour. CO2 (g) was bubbled through the mixture, and the reaction stirred at room temperature for 1 hour. The solvent was evaporated and water was added, the aqueous layer was washed with DCM (15 mL 3) and the pH adjusted to 3 by addition of 3M HCI. The mixture was extracted with DCM (15 mL 3) and the combined organic layers dried (Na2S04) and concentrated to give the title compound as a white solid (870 mg, 88%). LCMS-C: RT 2.26 min; m/z 195.1 (0878) [M+H]

The chemical industry reduces the impact on the environment during synthesis Methyl 4-iodo-3-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CTXT PTY LTD; BERGMAN, Ylva Elisabet; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; CAMERINO, Michelle Ang; WALKER, Scott Raymond; LAGIAKOS, H. Rachel; FEUTRILL, John; STEVENSON, Graeme Irvine; STUPPLE, Paul Anthony; (222 pag.)WO2016/34673; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 5471-81-8, The chemical industry reduces the impact on the environment during synthesis 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, I believe this compound will play a more active role in future production and life.

(a) Synthesis of methyl 3-methyl-4-(3-ethyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyloxy)benzoate In a manner similar to Example 1(a), by the reaction of 2.1 g (8.7 mmol) of 3-ethyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol with 2 g (7.2 mmol) of methyl 3-methyl-4-iodobenzoate, 2.18 g (79%) of the expected methyl ester was obtained in the form of a pale 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; Centre International de Recherches Dermatologiques Galderma; US6162815; (2000); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

General procedure: Table 2, example 4 PdOAc2 (3.4 mg, 0.015 mmol), cesium carbonate (293 mg, 0.900 mmol), and tris(4-methoxyphenyl)phosphine (12 mg, 0.033 mmol) were combined in dioxane (2 mL) and stirred for 15 min at room temperature under an atmosphere of nitrogen. Then 6-chloro-3-iodo-2-methylpyridine (76 mg, 0.30 mmol), O-benzoyl morpholine (69 mg, 0.330 mmol), methylboronic acid(20 mg, 0.33 mmol), and bicyclo[2.2.1]hept-2-ene (28 mg,0.30 mmol) were added as a solution in dioxane (2 mL) to the previously prepared solution of catalyst and base. The reaction was sealed and heated to 100C for 18 h. The reaction mixturewas cooled to room temperature and filtered through a pad of celite eluting with ethyl acetate. The eluent was concentrated and the residue was puried by silica gel chromatography (ISCO 24 gsilica cartridge; 0-30% ethyl acetate in hexanes) to provide4-(6-chloro-2,3-dimethylpyridin-4-yl)morpholine (41 mg, 60%yield) as a colorless oil.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Wilson, Jonathan E.; Tetrahedron Letters; vol. 57; 46; (2016); p. 5053 – 5056;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

Methyl 4-formyl-3-methylbenzoate (1616-18a). To a solution of methyl 4-iodo-3- methylbenzoate (1.0 g, 3.6 mmol) in THF (24 mL, 0.15 M) at -15C was added isopropylmagnesium chloride (7.2 ml, 14.5 mmol, 4.0 equiv). The reaction mixture was allowed to continue stirring at -15C for 2 hrs before N,N-dimethylformamide (1.4 ml, 18mmol, 5.0 equiv) was added. The mixture was warmed to room temperature over a period of 1 hr. At this time the reaction was quenched with HC1 and extracted with EtOAc (3x). The combined organic layers were washed with brine and dried over MgSO4, filtered and concentrated in vacuo.Purification was achieved using flash column chromatography on Si02 (Hexanes/EtOAc:6/1) to yield a white solid (0.45 g, 70 %) which was taken on without further purification.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; EMORY UNIVERSITY; TRAYNELIS, Stephen F.; MULLASSERIL, Praseeda; GARNIER, Ethel C.; LIOTTA, Dennis C; ZIMMERMAN, Sommer; WO2014/25942; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. Recommanded Product: Methyl 4-iodo-3-methylbenzoate

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.), N-(2,3-epoxypropyl)phthalamide (0.6 mmol, 3.0 equiv.) and dried 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 added. Heat to 80 C for 24 hours. After cooling the reaction vessel to room temperature, it was quenched with water (10 mL) with methyl tert-butyl ether (3× 10 mL) was extracted, dried over Na2SO4, filtered and concentrated in vacuo. Purified by column chromatography, the eluent was petroleum ether: ethyl acetate = 2:1 (v/v),Obtained 42 mg of methyl 7-methyl-2-((1,3-dioxoisoindolin-2-yl)methyl)-2,3-dihydrobenzofuran-5-carboxylate (white solid, Yield 60%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5471-81-8, 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

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, Product Details of 5471-81-8

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%), methyl 3-methyl-4-iodobenzoate (0.2 mmol, 1.0 equiv.),(4R)-4-((3S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadehydro-1H-cyclopenta[a]phenanthrene- 17-yl)pentanoic acid (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 mixture was cooled to EtOAc EtOAc EtOAc m. Purified by column chromatography, the eluent was toluene: diethyl ether = 2:1 (v/v),(2R)-7-Methyl-2-(((4R)-4-((3S,8R,9S,10S,13R,14S,17R)-10,13-dimethylhexadecahydro-3) -Hydroxy-1H-cyclopentadieno[a]phenanthrene-17-yl)pentanoyl)oxy)methyl)-2,3-dihydrobenzofuran-5-carboxylic acid methyl ester 99 mg (colorless oily liquid) ,Yield 85%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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

Reference of 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.

A solution of methyl 4-iodo-3-methylbenzoate (21 .7 mmol, 6 g) in dry THF (120 mL) was purged with argon. The solution was cooled to -155C, /-PrMgCI (2M in THF, 108.5 mmol, 54.25 mL), and DMF (130.2 mmol, 10 mL) were added and the reaction was stirred for 2 h at -155C and then warmed to 255C and allowed to react for an additional hour. The reaction was quenched with aqueous 1 N HCI and extracted with EtAcO. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude was purified by flash chromatography on silica gel using an elution of 6% ethylacetate in hexanes to give methyl 4-formyl-3-methylbenzoate (3.08g .Yield: 80%). 1 H NMR (400 MHz, CDCI3) delta 10.35 (1 H, s), 8.00 (1 H, d, J=8Hz), 7.99 (1 H, s), 7.86 (1 H, d, J=8Hz), 3.95 (3H, s), 2.72 (3H, s) LC-MS: tR = 2.85 [M+H]+ = not ion (method 3).

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; ALMIRALL, S.A.; DRACONIS PHARMA, S.L.; LABORATORIOS DEL DR. ESTEVE, S.A.; AGUILAR, Nuria; FERNANDEZ, Joan, Carles; TERRICABRAS, Emma; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/149997; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com