Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 57381-62-1, name is Methyl 2-bromo-4-chlorobenzoate, 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 57381-62-1, Safety of Methyl 2-bromo-4-chlorobenzoate

50 g (200 mmol) of methyl-2-bromo-4-chlorobenzoate was dissolved in 0.5 L of tetrahydrofuran (THF) under a nitrogen atmosphere, 50.2 g (220 mmol) of dibenzofuran-4-ylboronic acid and 4.63 g (4.01 mmol) of tetrakis(triphenylphosphine)palladium were added thereto, and the mixture was agitated. Then, 59.0 g (401 mmol) of potassium carbonate saturated in water was added thereto, and the obtained mixture was heated and refluxed at 80 °C for 18 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM) and treated with anhydrous MgSO4 to remove moisture and then, filtered and concentrated under a reduced pressure. Then, a residue obtained therefrom was separated and purified through flash column chromatography, obtaining 56.5 g (80 percent) of the intermediate I-5. HRMS (70 eV, EI+): m/z calcd for C20H13ClO2S: 352.0325, found: 352.Elemental Analysis: C, 68 percent; H, 4 percent

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

Reference:
Patent; Cheil Industries Inc.; LEE, Han-Ill; YU, Eun-Sun; KANG, Dong-Min; KANG, Eui-Su; MIN, Soo-Hyun; YANG, Yong-Tak; OH, Jae-Jin; RYU, Dong-Kyu; LEE, Sang-Shin; JANG, Yu-Na; JEONG, Soo-Young; JO, Young-Kyoung; HAN, Su-Jin; HONG, Jin-Seok; EP2952511; (2015); A1;,
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Synthetic Route of 13195-64-7, 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. 13195-64-7 name is Diisopropyl malonate, 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.

To a solution of diisopropyl malonate (500 mg, 2.65 mmol, 1 equiv) and nitroso benzene (313 mg, 2.92 mmol, 1 equiv) in absolute ethanol (1.25 mL, 2.2M), a saturated ethanolic solution of NaOH was added dropwise until the blue color of the solution turns pale brown. The reaction mixture was allowed to stir for 10 minutes and the solvent was removed under reduced pressure and the crude product was purified by column chromatography to afford 39 as viscous yellow colored oily liquid (449 mg, 61 percent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diisopropyl malonate, and friends who are interested can also refer to it.

Reference:
Patent; WILLIAM MARSH RICE UNIVERSITY; KATTAMURI, Padmanabha Venkatesh; KURTI, Laszlo; (181 pag.)WO2018/213572; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl 3-(4-aminophenyl)acrylate

EXAMPLE 252 4-[14-(Trimethylsilyl)tetradecylamino]cinnamic acid A mixture of 5.0 g. ethyl 4-aminocinnamate, 9.14 g. of 14-(trimethylsilyl)tetradecyl bromide and 3.6 g. of powdered anhydrous potassium carbonate in hexamethylphosphoramide is heated for 20 hours at 60° C. The mixture is then cooled, diluted with water and extracted with ether. The combined ether extracts are dried, filtered and evaporated to provide ethyl 4-[14-(trimethylsilyl)tetradecylamino]cinnamate.

According to the analysis of related databases, 5048-82-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; US4670421; (1987); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 4630-80-2, name is Methyl cyclopentanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl cyclopentanecarboxylate

General procedure: In the glove box, a conjugated boronic acid pinacol borate (1.2 mmol, 304.8 mg) was added to a Schlick reaction tube.Ferrous (0.03mmol), sodium tert-butoxide (0.9mmol), removed from the glove box, and added ethyl hexanoate under nitrogen atmosphere(0.3 mmol, 43.3 mg), ethanol (0.3 mmol), then 2 ml of toluene was added, and after stirring for 5 minutes, the reaction tube was placed at 100 C.The reaction in the pot was carried out for 24 hours. After the reaction is completed, ethyl acetate extraction is added to the system, and the product is obtained by column chromatography, and the yield is73%.

The synthetic route of 4630-80-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Lanzhou Chemical Physics Institute Suzhou Institute; Liu Chao; He Zeyu; Zhu Qing; (10 pag.)CN109734737; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)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. COA of Formula: C11H14O4

6,7-Dimethoxy-1-methylisoquinolin-3-ol CCH 18060 To a solution of methyl 2-(3,4-dimethoxyphenyl)acetate SLA 28134 (23.82 g, 113.30 mmol) in acetic anhydride (57 mL) at 0 C. in a 1 L round-bottomed flask equipped with a magnetic stirrer under N2 was added perchloric acid (70% solution in water, 11.3 mL) over a period of 30 min. The reaction mixture was then allowed to warm up to RT, stirred for a further 45 min and diluted with Et2O (450 mL). The solid was then filtered and washed several times with Et2O (6*15 mL) to give after drying under vacuum a dark yellow solid (27.97 g, 74% yield). To a suspension of the above solid (11.09 g, 34.58 mmol) in H2O (60 mL) in a 500 mL 3-neck round-bottomed flask equipped with a dropping funnel and a magnetic stirrer in an ice bath was added dropwise conc. NH4OH (90 mL) and the reaction mixture was stirred at RT for 1 h, after which the solid was filtered and washed with cold water (4*15 mL). After drying under high vacuum, 6,7-dimethoxy-1-methylisoquinolin-3-ol CCH 18060 was isolated as a yellow solid (7.53 g, 99% yield). MW: 219.24; Yield: 74%; Yellow solid; Mp ( C.): 283 (dec.). Rf: 0.2 (cyclohexane:EtOAc=2:1). 1H-NMR (DMSO d6, delta): 2.68 (s, 3H, CH3), 3.85 (s, 3H, OCH3), 3.86 (s, 3H, OCH3), 6.51 (s, 1H, ArH), 6.97 (s, 1H, ArH), 7.12 (s, 1H, ArH), 10.69 (broad s, 1H, OH). 13C-NMR (DMSO d6, delta): 20.3, 55.6, 55.7, 99.5, 103.6, 103.8, 116.2, 138.0, 147.1, 152.0, 153.3, 159.0. MS-ESI m/z (rel. int.): 220 ([M+H]+, 100).

The synthetic route of 15964-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ExonHit Therapeutics SA; ALLERGAN, INC.; US2012/214837; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 431-47-0, name is Methyl 2,2,2-trifluoroacetate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 431-47-0

Trifluoroacetanilide (100 mg, 0.46 mmol), DMF (4 mL), potassium t-butoxide (153 mg, 1.37 mmol, 3 eq.) was added to the reaction mixture in turn, and stirred at room temperature for 5 minutes.After the potassium tert-butoxide was uniformly dispersed, methyl trifluoroacetate (0.19 mL, 1.84 mmol, 4 eq.) was slowly injected into the reaction flask, and after stirring at 60 C for 10 hours, stirring was stopped.Extract twice with ethyl acetate and distilled water, then wash with saturated NaCl solution.The organic phases were combined, and the organic phase was dried over anhydrous magnesium sulfate.Magnesium sulfate was removed by filtration, and the solvent was evaporated to give purified N-(4-methoxyphenyl)-N-methyltrifluoroacetamide (88 mg, yield 83%).

According to the analysis of related databases, 431-47-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Petrochemical College; Xiao Duoduo; Zheng Xin; Zeng Jiechun; Huang Jiawei; Zhou Rujin; Guan Ying; Liang Jieling; (8 pag.)CN109369506; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 33155-58-7, name is tert-Butyl 2-(4-Bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

To a stirring solution of 2-(5-chlorothiophen-2-yl)-4-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (1 eq.)in toluene (1.5 ml) was added Na01Bu (1.6 eq.), tert-butyl 2-(4-bromophenyl)acetate (1.5eq.) and BINAP (0.04 eq.). The resulting reaction mixture was degassed with argon for a period of 10 min. and Pd2dba3 (0.02eq.) was added and the mixture was degassed again. The reaction mixture was heated at 100C for16 h. At completion, the reaction mixture was concentrated and poured in DMF (2 mi).The inorganics were filtered and the residue was purified by prep-HPLC using aqueous ammonia method to give tert- butyl 2-(4-(2-(5-chlorothiophen-2-yl)-4-methyi-5H-pyrrolo[2,3-d]pyrimidin-7(6H)-yl)phenyl)acetate which was directly used for the next step. ).

According to the analysis of related databases, 33155-58-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; JAKOB, Florian; KONETZKI, Ingo; CRAAN, Tobias; NARDI, Antonio; HESSLINGER, Christian; WO2015/18534; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, 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 252881-74-6, HPLC of Formula: C13H27NO5

To 13-amino-4, 7, 10-trioxadodecanoic acid tert-butyl ester (0.80 g, 2.89 mmol) in 30 mL of dioxane was 10 ml of HCl (36%) with stirring. After 0.5 h TLC analysis revealed that the reaction was complete, the reaction mixture was evaporated, and co-evaporated with EtOH and EtOH/Toluene to form the title product in HCl salt (>90%pure, 0.640 g, 86%yield) without further purification. ESI MS m/z+ C 9H 20NO 5 (M+H) , cacld. 222.12, found 222.20.

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; HANGZHOU DAC BIOTECH CO., LTD; ZHAO, Robert Yongxin; ZHUO, Xiaotao; YANG, Qingliang; ZHAO, Linyao; HUANG, Yuanyuan; YE, Hangbo; YANG, Chengyu; LEI, Jun; GAI, Shun; GUO, Huihui; JIA, Junxiang; BAI, Lu; XIE, Hongsheng; ZHOU, Xiaomai; GUO, Zhixiang; LI, Wenjun; CAO, Mingjun; ZHENG, Jun; YE, Zhichang; YANG, Yanlei; (325 pag.)WO2020/6722; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: trans-Ethyl 4-hydroxycyclohexanecarboxylate

To a solution of ethyl 4-hydroxycyclohexane-1-carboxylate (10 g, 58.06 mmol) in dichloromethane (25 mL) was added triethylamine (13 g, 128.47 mmol) slowly at room temperature. After stirring for additional 20 min, TBDMSC1 (24.9 g, 87.09 mmol) was slowly added. The resulting reaction mixture was then stirred at room temperature for 40 h. The reaction mixture was quenched by the addition of water (100 mL) and extracted with dichloromethane (100 mL×2). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in hexane (1% to 10% gradient) to yield ethyl 4-[(tert-butyldimethylsilyl)oxy]cyclohexane-1-carboxylate as yellow oil (7.5 g, 45%).

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; Merck Patent GmbH; SHERER, Brian A.; (167 pag.)US2016/75711; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 1459-96-7,Some common heterocyclic compound, 1459-96-7, name is Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, molecular formula is C12H18O4, 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.

At atmospheric conditions, 0.1 g of the Milstein catalyst precursor [2-(Di-tert- butylphosphinomethyl)-6- (0259) (diethylaminomethyl)pyridine]carbonylchlorohydridoruthenium(ll), 30 mg of potassium hydroxide, 2.5g of dimethyl bicyclo[2.2.2]octane-1 ,4-dicarboxylate and 50 imL of p- xylene were added to a 100 imL autoclave reactor. The reactor was then purged three times by pressurizing with nitrogen to 200 psig, then venting the pressure to atmospheric each time. The reactor was then purged three times by pressurizing with hydrogen to approximately 300 psig, then venting the pressure to atmospheric each time. Agitation at 800 rpm was then commenced, and hydrogen was then added to bring the pressure to 750 psig. The temperature was then increased to 140 C while allowing pressure to rise. After the temperature reaches 140 C, the hydrogen pressure was increased to 1000 psig. These conditions (140 C and 1000 psig) were held for 8 hours of reaction. After 8 hours of reaction, the agitation was stopped and the heat turned off to let the autoclave start cooling. After cooling to room temperature, pressure was released, and the contents were purged with nitrogen gas and vented. The solution was finally discharged from the autoclave and analyzed by GC-MS and 1H NMR. The conversion of dimethyl bicyclo[2.2.2]octane-1 ,4-dicarboxylate is 94%; the selectivity of bicyclo[2.2.2]octane-1 ,4-diyldimethanol is 93%; and the selectivity of methyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-1 -carboxylate is 7%.

The synthetic route of 1459-96-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EASTMAN CHEMICAL COMPANY; HU, Yue, Rachel; HEMBRE, Robert, Thomas; TUSTIN, Gerald, Charles; LIU, Zhufang; ADAMS, Steven, J.; CLARKSON, Jasper, Randle; (59 pag.)WO2019/75004; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics