Tag: M.W=200-300

Application of 148547-19-7, 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. 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

[00156] Step 1 : To a solution of methyl 4-bromo-3-methylbenzoate (50 g, 219 mmol) in THF (500 mL) at 0 C was added lithium aluminum hydride (262 mL of 1 M solution in THF, 262 mmol) over 15 min. After stirring for 20 min, water (50 mL) was added dropwise, followed by 1 M NaOH (50 mL), and water (50 mL). The reaction mixture was filtered through Celite and concentrated in vacuo. The resulting residue was azeotroped once with toluene, then dissolved in DCM, dried over Na2S04, filtered and the solvent removed in vacuo to provide (4-bromo-3-methylphenyl)methanol as a colorless solid (42 g, 96% yield). XH NMR (400 MHz, DMSO-i¾) delta 7.51 (d, J= 8.1 Hz, 1H), 7.29 (s, 1H), 7.07 (d, J= 8.1 Hz, 1H), 5.23 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 5.7 Hz, 2H), 2.33 (s, 3H).

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; BINCH, Haley, Marie; HURLEY, Dennis, James; CLEVELAND, Thomas; JOSHI, Pramod; FANNING, Lev Tyler, Dewey; PINDER, Joanne; O’DONNELL, Michael; VIRANI, Anisa, Nizarali; KNEGTEL, Ronald, Marcellus Alphonsus; DURRANT, Steven, John; YOUNG, Stephen, Clinton; PIERRE-HENRI; KAY, David; REAPER, Philip, Michael; WO2011/143426; (2011); A1;,
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Reference of 87808-49-9, 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. 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Preparation of 2-(2-bromo-4-methylphenyl)propan-2-ol To a solution of methyl 2-bromo-4-methylbenzoate (4 g, 18 mmol) cooled at 0 C. was added methylmagnesium bromide (17.5 ml, 52.6 mmol) dropwise. The mixture was allowed to warm to rt and stirred overnight. Then it was quenched with aq. NH4Cl and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated to provide the product (3.5 g, yield 85%). TLC analysis (silica gel plate, EA_PE=10%): Rf=0.5.

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-4-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; AKAMA, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131017; (2013); A1;,
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Application of 24398-88-7, 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. 24398-88-7, name is Ethyl 3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Production Example 13 To a mixture of 85 mg of palladium acetate, 350 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and 15 mL of toluene were added 1.8 mL of ethyl 3-bromobenzoate, 1.02 g of 2-nitroaniline and 4.81 g of cesium carbonate, followed by stirring at 110 C. for 5 hours. The reaction solution was allowed to cool, 50 mL of ethyl acetate was added thereto to remove insoluble materials, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate-hexane=1:9) to obtain 2.10 g of ethyl 3-[(2-nitrophenyl)amino]benzoate as an light orange oily substance.

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, Ethyl 3-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Furutani, Takashi; Enjo, Kentaro; Kikuchi, Aya; Kuromitsu, Sadao; Ideyama, Yukitaka; Suzuki, Tomoyuki; Kurihara, Ryoko; US2011/282066; (2011); A1;,
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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. 17100-63-9, name is Methyl 4-bromo-3-methoxybenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 4-bromo-3-methoxybenzoate

To a stirred solution of methyl 4-bromo-3-methoxybenzoate (11.2 g) in THF (130 mL), methanol (45 mL) and water (45 mL) was added a 1 M solution of lithium hydroxide in water (140 mL). The mixture was stirred at room temperature for 1 h. The solvent was removed in vacuum. Water was added and 1 N hydrochloric acid was added with ice bath cooling until pH 4 was reached. The precipitated solid was collected by filtration, washed with water and dried in vacuum to give 10.1 g of the title compound, that was used without further purification. 1H-NMR (300MHz, DMSO-d6): delta [ppm] = 3.87 (s, 3H), 7.42 (dd, 1 H), 7.50 (d, 1 H), 7.68 (d, 1 H), 13.21 (br. s., 1 H).

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; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; MAIS, Franz-Josef; WO2014/9219; (2014); A1;,
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Some common heterocyclic compound, 1245643-11-1, name is Methyl 3,4-diamino-5-bromobenzoate, molecular formula is C8H9BrN2O2, 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. Quality Control of Methyl 3,4-diamino-5-bromobenzoate

At -40C, 2,2-dihydroxy-acetic acid (85.61 g; 93Ommol) in H20 (35 mL) was added dropwise to a solution of methyl-3,4-diamino-5-bromobenzoate (190 g; 775.28 mmol) in MeOH (2 L). Then, the reaction mixture was allowed to warm to rt and stirred for2h. The solid was filtered, washed with Et20 and dried under vacuum to give 214 g (98%) of a mixture of two intermediates la and lb (ratio 85/l5 by 1H NMR).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1245643-11-1, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; QUEROLLE, Olivier, Alexis, Georges; BERTHELOT, Didier, Jean-Claude; MEYER, Christophe; WILLOT, Matthieu, Philippe, Victor; MEERPOEL, Lieven; (384 pag.)WO2017/60406; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, belongs to esters-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 106896-49-5, category: esters-buliding-blocks

To a 250 rnL rmmd bottom flask purged with and maintained under Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
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Application of 14273-90-6,Some common heterocyclic compound, 14273-90-6, name is Methyl 6-bromohexanoate, molecular formula is C7H13BrO2, 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: Typical procedure: Under a dry argon atmosphere, a solution of imidazole (Im, 2.05g, 30.1mmol) in dry THF (10mL) was added dropwise to stirred potassium tert-butoxide (3.36g, 29.9mmol) in dry THF (40mL) at 0C. The resulting reaction mixture was stirred for 2h, a solution of 5a (5.46g, 30.2mmol) in dry THF (10mL) was added dropwise. After refluxing the resulting mixture for 16h, it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. After dissolving the residual liquid in dichloromethane, this solution was washed with water and brine several times, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluted with a mixed solvent of chloroform/methanol (10/1v/v). The fraction with an Rf value of 0.45 was collected and dried under reduced pressure to afford 1-[3-(methoxycarbonyl)propyl]imidazole

The synthetic route of 14273-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ichikawa, Tsukasa; Wako, Tsuyoshi; Nemoto, Nobukatsu; Reactive and functional polymers; vol. 99; (2016); p. 1 – 8;,
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Adding a certain compound to certain chemical reactions, such as: 7686-78-4, name is Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, belongs to esters-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 7686-78-4, Product Details of 7686-78-4

Preparation method: In air atmosphere,Add 0.2 mmol of N-pyrimidindolline compound to the microwave reaction tube,0.24 mmol of ethylene cyclopropane compound,0.003 mmol of [Ru (p-cymene) Cl2] 2, 0.06 mmol of 1-adamantanic acid,0.04 mmol of silver hexafluoroantimonate,Microwave at 50 C for 2 hours;After completion of the reaction, rinse with ethyl acetate.Chromatographic separation after concentration under reduced pressure (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0/100 to 100/0)Dried to a pale yellow oil,The yield was 76% and E / Z> 20: 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Zhengzhou University; Henan Communication Polytechnic College; Zhu Xinju; Wang Qiuling; Xie Xiaona; Zhang Xiaojie; Yan Jing; Xu Yan; Hao Xinqi; Song Maoping; (15 pag.)CN110551106; (2019); A;,
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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 115118-68-8,Some common heterocyclic compound, 115118-68-8, name is Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate, molecular formula is C14H24O6, 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.

Intermediates Ia and Ib are prepared by the methods described in literatures. Dissolve 15 g of intermediate Ibin 200 mL of ethanol, add 30 mL of NaOH (12 g, 0.3mol) aqueous solution, reflux the reaction solution for 3 hours, filterit in vacuum to obtain white solid and wash it with ethanol for 3 times to obtain intermediate Ic.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate, its application will become more common.

Reference:
Patent; Southeast University; GOU, Shaohua; EP2913335; (2015); A1;,
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