Month: March 2021

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 140-39-6 as follows. Safety of p-Tolyl Acetate

Acetic acid(4-methyl) phenolate 50.0gSoluble in 500ml of carbon tetrachloride, add 4.0g BPO,Stirring at 50 C,Add 71.5g NBS ((4-methyl) phenolate (II) acetate and NBS in 3 batches,The molar ratio of BPO was 1:1.2:0.05), and the reaction was kept for 3 hours. Filtering,The filtrate was concentrated under reduced pressure.The orange-red oil was added dropwise to petroleum ether and stirred to disperse, and a solid precipitated. After suction filtration, the filtrate was washed with water.After drying, it was concentrated under reduced pressure to give (4-bromomethylene) phenyl ester (III), 68.3 g.Yield 89.2%,

According to the analysis of related databases, 140-39-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hubei Guangchen Pharmaceutical Co., Ltd.; Hubei University; Wuhan Institute of Technology; Wang Kai; Liu Dan; Zhao Yimei; Jiang Jun; Kuang Weidong; Zhou Ji; Wu Fengshou; Yang Fang; (7 pag.)CN108640834; (2018); A;,
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Related Products of 37746-78-4, 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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, This compound has unique chemical properties. The synthetic route is as follows.

Preparation No.61: Preparation of (ii)-ethyl 4-(3-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4- oxadiazol-5-yl)-2-methylphenoxy)but-2-enoate; A 50 mL reaction vial equipped with septa cap outfitted with nitrogen inlet needle was charged with 3-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)-2-methylphenol (0.350 g, 1.015 mmol) and potassium carbonate (0.351 g, 2.54 mmol) in acetone (5.08 mL) to give a colorless suspension. (E)-ethyl 4-bromobut-2-enoate (0.275 mL, 2.030 mmol) was added dropwise via syringe. The resulting suspension was allowed to stir at RT for about 2 days. The reaction mixture was diluted with EtOAc and the solution was washed with 1M HC1 solution (1 x 50 mL), saturated NaHCC>3 solution (1 x 50 mL), and saturated NaCl solution (1 x 50 mL). The organic phase was dried over MgSC>4, filtered and concentrated to give 540 mg of a solid. The sample was purified via automated silica gel chromatography (10%-20% EtOAc : Heptane; EA -40g column, 18 x 150 mm test tubes). The fractions containing product were combined and concentrated to afford (E)-ethyl 4-(3-(3-(3-chloro-4- isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)-2-methylphenoxy)but-2-enoate (353 mg, 76%) as a solid. LC/MS (Table 1, Method k) Rt = 1.98 min, m/z 457 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis (E)-Ethyl 4-bromobut-2-enoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R.; WO2011/71570; (2011); A1;,
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Synthetic Route of 18927-05-4,Some common heterocyclic compound, 18927-05-4, name is Methyl 3-Methoxyphenylacetate, molecular formula is C10H12O3, 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.

Nitrobenzene (0.4 mmol), methylmethoxyphenylacetate (0.2 mmol),Dimethyl sulfoxide (0.5 mL) and sodium tert-butoxide (0.4 mmol) were successively added to the reaction flask and the reaction was carried out at 45 C for 8 hours. The reaction product was separated from the reaction solution by adding water, dilute hydrochloric acid and ethyl acetate, and the product was isolated by silica gel column chromatography. The yield was 43%, yellow solid,

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

Reference:
Patent; Changsha University of Science and Technology; Li Jiangsheng; Yang Fan; Yang Qian; Li Zhiwei; Chen Guoqin; (8 pag.)CN107033006; (2017); A;,
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Related Products of 1214334-90-3, 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. 1214334-90-3, name is Methyl 2-bromo-4-(trifluoromethyl)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: 2-Cvclopropyl-4-trifluoromethyl-benzoic acid methyl esterTo a solution of 400 mg (1.413 mmol) 2-bromo-4-trifluoromethyl-benzoic acid methyl ester ,146 mg (1.696 mmol) cyclopropyl boronic acid, 1.21g (4.946 mmol) tri-potassium phosphate monohydrate, 40.9 mg (0.141 mmol) tricyclohexyl phosphine in 6 ml toluene and 0.3 ml water under nitrogen at room temperature, was added 15.9 mg (0.0707 mmol) palladium acetate. The mixture was stirred in a 100 0C oil bath for 4 hours and overnight at room temperature under nitrogen. The mixture was cooled to room temperature. Water was added and the mixture extracted with ethyl acetate. The organic layer was washed once with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified on silica gel (eluent: heptane/ethyl acetate 0 to 10 %) to provide 0.24 g (71 %) of the title compound as 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 2-bromo-4-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; KOLCZEWSKI, Sabine; PINARD, Emmanuel; WO2011/23667; (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. 99974-66-0, name is Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate, A new synthetic method of this compound is introduced below., name: Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate

A solution of alcohol Id (3.0 g) in 200 mL of dichloromethane was treated with Dess-Martin periodinane (1.2 eq, 7.06 g). The mixture was stirred for 2 h at room temp. The reaction was quenched by addition of aq saturated sodium thiosulfate soln (100 mL). The mixture was stirred for 20 min followed by addition of aq saturated sodium bicarbonate soln (100 mL). The mixture was further stirred for 20 min and extracted with ethyl acetate (500 mL). The aqueous layer was back extracted with ethyl acetate (250 mL). The combined organic layers were washed with aq saturated sodium bicarbonate (2 x 80 mL) and brine (80 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in rotavap. The product was purified on silica gel (Biotage75-M column; gradient: 0 to 30% ethyl acetate in hexanes) to afford the product (5.14 g; 96 %) 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:
Patent; SCHERING CORPORATION; WO2009/8913; (2009); A2;,
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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. 1162676-00-7, name is Methyl 4-amino-3,5-difluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 4-amino-3,5-difluorobenzoate

EXAMPLE 5 2-[(3,5-Difluoro-4-amino)benzyl]imidazoline hydrochloride Starting with methyl-3,5-difluoro-4-amino benzoate and utilizing consecutively the procedures of Examples 1-4, affords the desired compound.

The synthetic route of 1162676-00-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott Laboratories; US4665095; (1987); A;,
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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 4934-99-0 as follows. category: esters-buliding-blocks

Step 1: methyl 3-(l,3-dioxo-2,3-dihydro-lH-isoindol-2-yI)cyclobutane-l- carboxylate: into a 1000-mL round-bottom flask, was placed a solution of methyl 3- hydroxycyclobutane-l -carboxylate (10 g, 76.88 mmol, 1.00 eq.) in tetrahydrofuran (500 mL), 2,3-dihydro-l H-isoindole-l,3-dione (13.2 g, 89.7 mmol, 1.20 eq.), triphenyl phosphine (23.6 g, 90.0 mmol, 1.20 eq.). This was followed by the addition of DEAD (21 g, 120.6 mmol, 1.50 eq.) dropwise with stirring. The resulting solution was stirred for 3 h at room temperature. The reaction was then quenched by the addition of water. The resulting solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 : 1). This resulted in 6 g (30%) of methyl 3-(l ,3-dioxo-2,3- dihydro-l H-isoindol-2-yl)cyclobutane-l -carboxylate as a white solid. NMR (300MHz, CDC ): delta 7.85-7.81 (m, 2H), 7.75-7.70 (m, 2H), 5.09-5.03 (t, J= 8.7 Hz, 1 H), 3.32-3.29 (m, 1 H), 3.18-3.10 (m, 2H), 2.67-2.59 (m, 2H), 1.31 -1.24 (m, 3H). LC-MS: (M+H)+ = 260.

According to the analysis of related databases, 4934-99-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (96 pag.)WO2016/105468; (2016); A1;,
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Some common heterocyclic compound, 37466-90-3, name is Ethyl 3,4-diaminobenzoate, molecular formula is C9H12N2O2, 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. HPLC of Formula: C9H12N2O2

General procedure: The mixture of ethyl 3,4-diaminobenzoate 19 (1 eq., 13.6 mmol), appropriate carboxyaldehyde (1,5 eq., 20.4 mmol) and p-toluenesulphonic acid (0,2 eq., 2.72 mmol) in toluene (150 mL) was heated at reflux with Dean-Stark apparatus for 6 h. After completion of the reaction (TLC control) the whole was concentrated and chromatographed on silica gel (heptane/ethyl acetate, gradient 0-60 % or CHCl3/MeOH 0-5 %). 4.1.14.1 Ethyl 2-(1,3-thiazol-2-yl)-1H-1,3-benzodiazole-6-carboxylate (20h) Synthesized from 19 (5,0 g, 27,7 mmol, 1 eq.) and 2-thiazolecarboxaldehyde (3,56 g, 30,5 mmol, 1,1 eq.). Solid, 7,4 g (yield 88 %). 1H NMR (300 MHz, CDCl3): delta 8.88 (d, J = 0.9 Hz, 1H), 8.01 (d, J = 3.2 Hz, 1H), 7.91 (d, J = 1.8 Hz, 1H), 7.83 (dd, J = 8.4, 1.9 Hz, 1H), 7.50 (dd, J = 3.2, 1.0 Hz, 1H), 6.75 (d, J = 8.4 Hz, 1H), 4.75 (s, 2H), 4.34 (q, J = 7.1 Hz, 2H), 1.39 (dd, J = 8.7, 5.6 Hz, 3H). API-ES: m/z 272.1 [M-H]-

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 37466-90-3, its application will become more common.

Reference:
Article; Moszczy?ski-P?tkowski, Rafa?; Majer, Jakub; Borkowska, Ma?gorzata; Bojarski, ?ukasz; Janowska, Sylwia; Mat?oka, Miko?aj; Stefaniak, Filip; Smuga, Damian; Bazyd?o, Katarzyna; Dubiel, Krzysztof; Wieczorek, Maciej; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 96 – 116;,
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140-39-6, name is p-Tolyl Acetate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C9H10O2

p-Tolyl acetate 2b (10 gm, 0.067 mol) was in 500 mL round bottom flask containing aluminium chloride (10.7 gm, 0.08 mol). It was heated on an oil bath at 140-150 C for 5-6 hr. The progress of the reaction was monitored by TLC using ethyl acetate:hexane as a solvent system. The reaction mixture was quenched with crushed ice and obtained solid product was extracted with ethyl acetate (2¡Á50 mL). The organic extracts were washed with brine solution (2¡Á15 mL) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to afford the corresponding crude compounds. The obtained compound 3b was recrystallized using aq. ethanol. Yield 92%. M.p. 45-48 C.

The synthetic route of 140-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shaikh, Mubarak H.; Subhedar, Dnyaneshwar D.; Khedkar, Vijay M.; Jha, Prakash C.; Khan, Firoz A. Kalam; Sangshetti, Jaiprakash N.; Shingate, Bapurao B.; Chinese Chemical Letters; vol. 27; 7; (2016); p. 1058 – 1063;,
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Reference of 169044-96-6, 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. 169044-96-6, name is Methyl 2-amino-5-bromo-4-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of compound 35 (500 mg, 1.92 mmol) inDMF (10 mL) were added 4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane (452 mg,2.31 mmol), Pd(dppf)2Cl2 (140 mg, 0.19 mmol) andCs2CO3 (1253 mg, 3.85 mmol). The mixture was stirred at70 C for 24 h with the protection of N2. It was cooled to RTand diluted with water and extracted with ethyl acetate. Thecombined organic layers were washed with brine. It wasdried over Na2SO4 and filtered. The filtrate was concentratedand the residue was purified by silica gel columnchromatography eluting with cyclohexane/EA (uv254,20:1) to give pale-yellow powder 36 (198.0 mg, 43.0%). 36:1H NMR (500 MHz, CDCl3) delta 7.63 (s, 1H), 7.35 (dd, J =8.6, 4.2 Hz, 4H), 6.94 (dd, J = 24.0, 8.6Hz, 4H), 6.07 (s,1H), 5.26 (t, J = 7.3 Hz, 1H), 4.99 (s, 2H), 4.64 (dd, J =13.8, 3.5 Hz, 1H), 4.41 (s, 1H), 3.81 (s, 3H), 3.80 (s, 3H),3.19 (d, J = 7.3 Hz, 2H), 2.78 (dd, J = 16.1, 13.9 Hz, 1H),2.65 (dd, J = 16.2, 2.7 Hz, 1H), 1.72 (s, 3H), 1.69 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-5-bromo-4-methoxybenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yi, Jingyu; Du, Guoxin; Zhao, Yuanyuan; Zhang, Liuqiang; Li, Bo; Zhu, Weiliang; Huang, Cheng; Li, Yiming; Guo, Fujiang; Medicinal Chemistry Research; vol. 27; 7; (2018); p. 1851 – 1862;,
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