Category: 35450-36-3

Application of 35450-36-3,Some common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, molecular formula is C9H9BrO3, 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 an argon atmosphere, a solution of 125.1 g of 2-bromo-5-methoxybenzoic acid methyl ester (1) in tetrahydrofuran (216 mL) was added to 1160 mL of a tetrahydrofuran solution of methylmagnesium bromide (1.1 mol / L) at 1 to 11 C. Was added dropwise over 1 hour 45 minutes.The ice water bath was removed and stirred at room temperature (~ 25 C.) for 19.5 hours.The reaction solution was added dropwise to an ammonium chloride aqueous solution (NH 4 Cl 200 g / H 2 0 800 g) at 5 to 23 C. over 5 minutes,1000 g of toluene was added and the mixture was separated into an organic layer and an aqueous layer.After washing the organic layer with 1000 g of water, it was separated into an organic layer and an aqueous layer, and the organic layer was concentrated under reduced pressure.250 mL of a mixed solution of ethyl acetate-heptane (1/9, v / v) was added to 136 g of the obtained crude product, and the mixture was stirred at 22 to 25 C. for 16 hours.The resulting slurry was filtered with suction and washed with 125 mL of a mixed solution of ethyl acetate-heptane (1/9, v / v).The obtained solid was dried under reduced pressure (40 C., 1 hour 15 minutes)To obtain 90.6 g (yield 72.4%) of white solid 2- (2-bromo-5-methoxyphenyl) propan-2-ol (2).

The synthetic route of 35450-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; Shirokawa, Shinichi; Shibata, Tsuyoshi; Kimura, Yoshihiro; Oi, Takahiro; Tanimoto, Toshihide; Wada, Hisaya; (42 pag.)JP2017/105748; (2017); A;,
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Synthetic Route of 35450-36-3, 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. 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of Cs2CO3 (2 mmol) in H2O (5 mL) were added methyl 2-bromobenzoate (1a, 1 mmol), 1H-pyrazol-5-amine (2a, 1.2 mmol), and CuI (0.2 mmol). The mixture was stirred at 100 C under nitrogen atomasphere until a complete conversion as indicated by TLC. It was cooled to room temperature and then extracted with ethyl acetate. The combined organic phase was dried over anhydrous Na2SO4, and concentrated under vacuum. The crude product was purified by column chromatography eluting with petroleum ether/ethyl acetate (3:1) to give 3a. Products 3b-3t and 6 were obtained in a similar manner.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-5-methoxybenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Xinying; Gao, Lin; Wang, Zhangxin; Fan, Xuesen; Synthetic Communications; vol. 45; 21; (2015); p. 2426 – 2435;,
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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. 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 35450-36-3

Example 1; Part A: Compound 1 (20.0 g, 81.61 mmol), trimethylboroxine (13.36 ml_, 97.93 mmol),Pd(dppf)CI2 (1.0 g, 1.36 mmol), dioxane (350 ml_), water (50 ml_), and cesium carbonate (22.5 g, 163 mmol) were stirred at 110 0C (oil bath) under nitrogen for 16 hours. After cooling, the solid was removed by filtration. The solution was concentrated and purified by sgc (10:1 EtOAc/hexanes) to give 2 (12.1 g,80%).

The synthetic route of 35450-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; KOZLOWSKI, Joseph, A.; YU, Wensheng; WONG, Michael, K.C.; KIM, Seong-Heon; TONG, Ling; LAVEY, Brian, J.; SHANKAR, Bandarpalle, B.; YANG, De-Yi; FELTZ, Robert; KOSINSKI, Aneta, Maria; ZHOU, Guowei; RIZVI, Razia, K.; DAI, Chaoyang; FIRE, Luke; GIRIJAVALLABHAN, Vinay, M.; LI, Dansu; POPOVICI-MULLER, Janeta; RICHARD, Judson, E.; ROSNER, Kristin, E.; SIDDIQUI, M., Arshad; YANG, Liping; WO2010/54279; (2010); A1;,
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Synthetic Route of 35450-36-3, A common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, molecular formula is C9H9BrO3, 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.

Add CuI (19.45 mg), PdCl2 (PPh3) 2 (105.29 mg) to the round bottom flask,Under nitrogen, methyl 2-bromo-5-methoxybenzoate (1.68 mL), phenylacetylene (0.66 mL), Et3N (2.08 mL), and THF (15 mL) were added in this order, and the reaction was performed at 55 C for 6 h.TLC tracks the progress of the reaction; after the reaction is complete, the resulting reaction solution is cooled to room temperature,Then filtered through diatomaceous earth and purified by column chromatography to obtain the first intermediate;Dissolving the first intermediate in methanol, adding a 10% NaOH solution, and stirring at room temperature for 2 h,TLC tracks the progress of the reaction; after the reaction is complete, adjust the pH of the resulting reaction solution to dilute 2-3 with dilute hydrochloric acid,The obtained solid was filtered and purified by recrystallization to obtain a second intermediate;Add SOCl2 to the second intermediate and reflux at 90 C for 2 h.TLC followed the progress of the reaction; after the reaction was completed, SOCl2 was removed to obtain a third intermediate;At 0 C, add N-methoxyamine and potassium carbonate to 15 mL of ethyl acetate in this order.(EA) and water (EA: water volume ratio = 2: 1), the third intermediate was added dropwise after 10 min, and the reaction was performed at room temperature for 1 h.TLC tracks the progress of the reaction; after the reaction is complete, it is extracted with EA and H2O.Dry over anhydrous sodium sulfate and recrystallize to obtain N-methoxy-5-methoxy-2-phenylethynylbenzamide (1h);

The synthetic route of 35450-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunan University of Science and Technology; Xie Wenlin; Liu Renzhi; Qiu Guanyinsheng; (15 pag.)CN110590641; (2019); A;,
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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. 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H9BrO3

Under an argon atmosphere, 2.300 g (approx. 10.298 mmol) of the compound from example 51A was dissolved in 20 ml toluene and 2.103 g (8.585 mmol) of methyl-2-bromo-5-methoxybenzoate, 2.551 g (12.014 mmol) potassium phosphate, 0.346 g (1.159 mmol) of (2-biphenyl)di-tert.- butylphosphine and 0.173 g (0.772 mmol) of palladium(II) acetate were added. The mixture was boiled under reflux overnight. After cooling, it was extracted with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate and concentrated in a rotary evaporator at reduced pressure. The residue was purified by preparative HPLC (eluent: acetonitrile/water, gradient 10:90 ? 90:10). We obtained 135 mg (4% of theor.).LC-MS (method 4): R, = 1.28 min; MS (EIpos): m/z = 368 [M+H]+.1H-NMR (400 MHz, DMSO-D6): delta [ppm] = 2.20 (s, 3H), 3.70 (s, 3H), 3.80 (s, 3H), 3.84 (s, 3H), 6.07 (s, IH), 7.04 (dt, IH), 7.11 (dd, IH), 7.16-7.24 (m, 2H), 7.30 (d, IH), 7.34 (dd, IH), 7.41-7.46 (m, IH), 9.14 (sbr, IH).

The synthetic route of 35450-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; KAST, Raimund; GRIEBENOW, Nils; MEIER, Heinrich; KOLKHOF, Peter; ALBRECHT-KUePPER, Barbara; NITSCHE, Adam; STASCH, Johannes-Peter; SCHNEIDER, Dirk; TEUSCH, Nicole; RUDOLPH, Joachim; WHELAN, James; BULLOCK, William; PLEASIC-WILLIAMS, Susan; WO2010/20363; (2010); A1;,
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Ester – an overview | ScienceDirect Topics

Application of 35450-36-3, A common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, molecular formula is C9H9BrO3, 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.

General procedure: A sealed tube of 25 mL equipped with a magnetic stir bar was charged with alkynes (0.20 mmol), 2-bromobenzoic esters (0.22 mmol), CuI (0.02 mmol, 10 mol%), NaOH (0.4 mmol, 2 equiv) and CH3CN (1.0 mL). The reaction mixture was stirred at 100 C for 24 h. The reaction was monitored by GC or GC-MS. After completion of the reaction, the reaction mixture was cooled to room temperature, then washed with saturated NH4Cl aqueous solution (5.0 mL), and extracted with CHCl3 (3 * 5.0 mL). The combined organic phases were dried over Na2SO4 (anhydrous), concentrated in vacuum. The crude product was purified by flash column chromatography (eluent: ethyl acetate/petroleum ether = 1/20-1/10) on silica gel to afford the desired product.

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; Sun, Mengli; Su, Lebin; Dong, Jianyu; Liu, Long; Zhou, Yongbo; Yin, Shuang-Feng; Tetrahedron Letters; vol. 58; 25; (2017); p. 2433 – 2437;,
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Ester – an overview | ScienceDirect Topics

Synthetic Route of 35450-36-3, 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. 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A sealed tube of 25 mL equipped with a magnetic stir bar was charged with alkynes (0.20 mmol), 2-bromobenzoic esters (0.22 mmol), CuI (0.02 mmol, 10 mol%), NaOH (0.4 mmol, 2 equiv) and CH3CN (1.0 mL). The reaction mixture was stirred at 100 C for 24 h. The reaction was monitored by GC or GC-MS. After completion of the reaction, the reaction mixture was cooled to room temperature, then washed with saturated NH4Cl aqueous solution (5.0 mL), and extracted with CHCl3 (3 * 5.0 mL). The combined organic phases were dried over Na2SO4 (anhydrous), concentrated in vacuum. The crude product was purified by flash column chromatography (eluent: ethyl acetate/petroleum ether = 1/20-1/10) on silica gel to afford the desired product.

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 2-bromo-5-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sun, Mengli; Su, Lebin; Dong, Jianyu; Liu, Long; Zhou, Yongbo; Yin, Shuang-Feng; Tetrahedron Letters; vol. 58; 25; (2017); p. 2433 – 2437;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, 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. SDS of cas: 35450-36-3

A mixture of methyl 2-bromo-5-methoxybenzoate (3.0 g, 12.2 mmol), vinylboronic acid (2.26 g, 14.7 mmol), K2CC>3 (5.08 g, 36.72 mmol) and Pd(dppf)Cl2-DCM (500 mg, 0.61 mmol) in 1,4-dioxane/H2Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; FOITZIK, Richard, Charles; CAMERINO, Michelle, Ang; NIKOLAKOPOULOS, George; BOZIKIS, Ylva, Elisabet, Bergman; KERSTEN, Wilhelmus, Johannes, Antonius; WALKER, Scott, Raymond; HUBERT, Jonathan, Grant; (0 pag.)WO2020/2587; (2020); A1;,
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Application of 35450-36-3, 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 35450-36-3 as follows.

To a cold solution (ice water bath) of the methyl-2-bromo-5-methoxybenzoate (2.00 g, 8.16 MMOL) in DICHLOROMETHANE (15 mL) was added AIC13 (5.44 g, 40.8 MMOL) under argon, and the reaction temperature was maintained BELOW 10C using an ice-water bath. The light brown suspension was stirred for 10 min, then EtSH (3.02 mL, 40.8 MMOL) was added dropwise at such a rate that the reaction temperature was maintained BELOW 5C. After 2.5 h of stirring below 10C, the reaction mixture was slowly poured into ice water with agitation. The organic layer was separated, and the aqueous layer was extracted with DCM. The combined organic layers were washed with water, dried over MGS04, filtered and concentrated under reduced pressure to afford a light yellow oil which was used in the next step without further purification.

According to the analysis of related databases, 35450-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2004/50650; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, 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. Formula: C9H9BrO3

Step B 2-Bromo-5-methoxybenzyl alcohol Lithium aluminum hydride (1.3 eq) was added in portions to a solution of methyl 2-bromo-5-methoxy benzoate (1 eq) in diethyl ether (0.35 M) at 0 C. under N2 and the resulting mixture allowed to warm to RT with stirring for 5 h. Quenched with H2O (3*g LAH), followed sequentially by 15% NaOH solution (3*g LAH), a nd H2O (3*g LAH). The solution was filtered through a scintered glass funnel rinsing with diethyl ether and concentrated in vacuo to give 2-bromo-5-methoxybenzyl alcohol as a clear oil. EI-MS m/z 239, 241 (M+Na)+

The synthetic route of Methyl 2-bromo-5-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; US6514964; (2003); B1;,
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