Category: esters-buliding-blocks

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 206551-41-9 as follows. Application In Synthesis of Methyl 3-bromo-2-fluorobenzoate

Methyl 3-bromo-2-fluorobenzoate (500 mg, 2.15 mmol) dissolved in diethyl ether (15 mL) was cooled to 0 ¡ãC and treated with lithium aluminum hydride (81 mg, 2.13 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 6h. The reaction mixture was againcooled to 0 ¡ãC and methanol was added dropwise slowly followed by water. The reaction mixture wasdiluted with ethyl acetate and washed with water. The organic layer was concentrated to give (3-bromo- 2-fluorophenyl)methanol.

According to the analysis of related databases, 206551-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; APPLEBY, Todd; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; GUERRERO, Juan A.; JABRI, Salman Y.; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; NOTTE, Gregory; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (724 pag.)WO2018/195321; (2018); A1;,
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Reference of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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.

Chloro(1 ,1-dimethylethyl)dimethylsilane (115g; 0.76mol) was added in portions over 1 hour to a solution of ethyl 4-hydroxycyclohexanecarboxylate (118g; 0.68mol), imidazole(103g; 1.52mol) and dimethylformamide (400ml) stirred under an atmosphere of argon. A small exotherm was observed resulting in the reaction mixture temperature increasing to~40C. The mixture was stirred at room temperature overnight then poured into 10% citric acid solution (2L) and extracted with diethyl ether (2 x 800ml). The ether extracts were washed with water, brine and then dried (Na2SO4) and the solvent was removed to give the title compound as a oil (198.4g) 1H NMR delta (CDCI3, 400 MHz): 0.01 (6H, m), 0.85 (9H, s), 1.2 (3H, m), 1.3-1.5 (2H, m), 1.6 (2H, m), 1.85-2 (3H, m), 2.15-2.3 (1 H, m) 3.5 (0.4H, m) 3.86 (1 H, m) 4.1 (1 H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route trans-Ethyl 4-hydroxycyclohexanecarboxylate, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/107565; (2007); A1;,
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Synthetic Route of 3196-23-4, 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. 3196-23-4, name is Methyl 1-bromocyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

AD3 (R1 and R2 together formed a cyclohexyl ring) was mixed with BocNHOH in DMSO and treated with NaH (1 equiv.) at 50 0C overnight. After aqueous work up, the crude mixture was then treated with TFA to afford AD4 (R1 and R2 together formed a cyclohexyl ring) as the TFA salt.

The chemical industry reduces the impact on the environment during synthesis Methyl 1-bromocyclohexanecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; ZHU, Zhaoning; GREENLEE, William, J.; LI, Hongmei; VICAREL, Monica, L.; QIN, Jun; DHONDI, Pawan, Kumar; HUANG, Xianhai; PALANI, Anandan; LIU, Xiaoxiang; SUN, Zhong-Yue; JOSIEN, Hubert B.; XU, Ruo; COLE, David, James; BURNETT, Duane, A.; BENNETT, Chad, E.; MCCRACKEN, Troy, M.; MACCOSS, Malcolm; WO2010/56722; (2010); A1;,
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Electric Literature of 91-44-1, 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. 91-44-1 name is 7-(Diethylamino)-4-methyl-2H-chromen-2-one, 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.

General procedure: In a Schlenk tube, coumarin 1 (0.5mmol), dialkyl H-phosphite 2 (1.0mmol), AgNO3 (0.025mmol, 4.2mg) and Mg(NO3)2¡¤6H2O (0.25mmol, 64mg) were added and charged with Nitrogen (3 cycles). Anhydrous CH3CN (1mL) was then added. After heating in the oil bath at 100C for 6h (monitored by TLC), 5mL ethylacetate was added to dilute the reaction solution. The solution was filtrated, and the solvent was distilled under vacuum. The crude product was purified by silica gel column chromatography to give the desired product 3 using ethylacetate/petroleum ether (1:5 to 2:1) as eluant.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-(Diethylamino)-4-methyl-2H-chromen-2-one, and friends who are interested can also refer to it.

Reference:
Article; Yuan, Jin-Wei; Li, Yuan-Zhe; Yang, Liang-Ru; Mai, Wen-Peng; Mao, Pu; Xiao, Yong-Mei; Qu, Ling-Bo; Tetrahedron; vol. 71; 42; (2015); p. 8178 – 8186;,
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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. 207346-42-7, name is Methyl 2-amino-4,5-difluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H7F2NO2

methyl 2-amino-4,5-difluorobenzoate (40.0 g, 214 mmol) and NCS (25.9 g, 194 mmol) were suspended in DMF (10 mL) and heated at 95 C. for 30 min. Water and DCM were added to the mixture. The organic phase was separated. The aqueous phase was extracted with DCM (2 x 10 mL). The combined organic phases were dried, filtered and concentrated. The resulting residue was purified by normal phase chromatography (0 to 40% EtOAc in hexanes) to give compound 148a (11 g, 26% yield) as a white solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 207346-42-7.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXO GROUP LIMITED; YAMAWAKI, KENJI; YOKOO, KATSUKI; SATO, JUN; KUSANO, HIROKI; AOKI, TOSHIAKI; LIAO, XIANG MIN; PEARSON, NEIL DAVID; PENDRAK, ISRAIL; THALGI, REEMA; (373 pag.)JP6377570; (2018); B2;,
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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. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 18595-14-7

To a stirred and cooled (0 C) slurry of commercially available methyl 4-amino-3-methylbenzoate (2 g, 12.12 mmol) in 6 N HCl (12 mL) was added NaNO2 (0.92 g, 13.33 mmol) in water (2 mL) drop wise maintaining a temperature of <15 C during the addition. The mixture was stirred an additional 1.5 h affording a light yellow, homogeneous solution. To the mixture was carefully added 4.58 g (24.24 mmol) of anhydrous SnCl2. The temperature during the addition was kept <10 C. The mixture was stirred at 0 C for 1 h. The precipitated solid was collected by filtration, dried under vacuum to afford methyl 4-hydrazinyl-3-methylbenzoate hydrochloride 4 (1.75 g 81%) as a brown solid: mp 224-226 C; 1H NMR (CDCl3, 500 MHz) delta ppm 2.22 (s, 3H), 3.80 (s, 3H), 6.99 (d, J = 8.5 Hz, 1H), 7.70 (s, 1H), 7.77 (d, J = 8.5 Hz, 1H); MS (ESI): m/z calcd for C9H12N2O2 ([M+H]+) 181.0932; found 181.0911 ([M+H]+). The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings. Reference:
Article; Chiruta, Chandramouli; Zhao, Yanrong; Tang, Fangling; Wang, Tao; Schubert, David; Bioorganic and Medicinal Chemistry; vol. 21; 10; (2013); p. 2733 – 2741;,
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These common heterocyclic compound, 1188911-72-9, name is Methyl 3,3,3-trifluoro-2,2-dimethylpropanoate, 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. Quality Control of Methyl 3,3,3-trifluoro-2,2-dimethylpropanoate

[00444] To a -78 C solution of diisopropylamine (15 mL, 107 mmol) in THF (150 mL) was added n-BuLi (2.4 mol/L, 8 mL) dropwise. The reaction mixture was stirred for 30 minutes and a solution of methyl 3,3,3-trifluoro-2,2-dimethylpropanoate (3 g, 17.63 mmol) in acetonitrile (10 mL, 239 mmol) was added dropwise slowly. One hour later, the mixture was warmed slowly to rt and stirred for 2 hours. The mixture was quenched with saturated aqueous ammonium chloride solution (50 mL), and the resulting mixture was extracted with ethyl acetate (300 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/1) to give the title compound as a white solid (1.53 g, 48%). The compound was characterized by the following spectroscopic data: MS-ESI: (ESI, pos.ion) m/z: 180.1 [M+lfb; and ?H NMR (600 MHz, CDC13) 3.77 (s, 2H), 1.43 (s, 6H).-78 C

The synthetic route of Methyl 3,3,3-trifluoro-2,2-dimethylpropanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CHENG, Changchung; ZHANG, Yingjun; LIU, Bing; LONG, Bohua; CHEN, Yu; CHENG, Zhixin; (182 pag.)WO2016/8433; (2016); A1;,
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Electric Literature of 1128-76-3, 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. 1128-76-3, name is Ethyl 3-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The ethyl esters (0.15 mol; 2a-o) were taken in 250 mL round bottom flask.About 30 mL of methanol was added to the flask and homogenized by stirringat room temperature. Hydrazine hydrate (80%; 0.15 mol) was introduced to theflask drop wise and the reaction apparatus was refluxed for 5-6 hrs. Reactionprogress was confirmed by thin layer chromatography. n-Hexane and ethylacetate (3:2). At the end of reaction, excess of solvent was evaporated andresidue was poured into the ice cold water. Precipitates of acid hydrazides werefiltered, washed with water and dried. Re-crystallization of acid hydrazides wasperformed by using methanol.

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

Reference:
Article; Aziz-Ur-Rehman; Ahtzaz, Samreen; Abbasi, Muhammad Athar; Siddiqui, Sabahat Zahra; Rasool, Shahid; Ahmad, Irshad; Journal of the Chilean Chemical Society; vol. 62; 1; (2017); p. 3370 – 3375;,
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Electric Literature of 2967-66-0,Some common heterocyclic compound, 2967-66-0, name is Methyl 4-(trifluoromethyl)benzoate, molecular formula is C9H7F3O2, 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.

Step 2: To a solution of anhydrous hydrazine in anhydrous toluene is added methyl 4-(trifluoromethyl) benzoate (4). The reaction solution is heated at reflux for 18 hours under a nitrogen atmosphere. After cooling to 40-50C, the solvent is evaporated under reduced pressure. The resulting solid is recrystallized from tert-butyl methyl ether to give hydrazide (5) as a white solid.

The synthetic route of 2967-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Siga Technologies, Inc.; JORDAN, Robert; BAILEY, Thomas, R.; RIPPIN, Susan R.; DAI, Dongcheng; (69 pag.)EP3006425; (2016); 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. 3469-00-9, name is Methyl Diphenylacetate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Step 1 : Methyl 2.2-bis(4-nitrophenyl)acetate (8). Compound 7 (6 g, 26.5 mmol) was dissolved in fuming nitric acid (60 mL) and stirred at room temperature for 16 h. The reaction mixture was poured onto ice, the resulting light yellow sludge was separated out then dissolved in ether to provide a solid. Filtration afforded title compound 8 as a white solid (1.15 g, 14%). 1H NMR (DMSO-d6) delta (ppm):8.22 (d, J = 9.0 Hz, 4H), 7.65 (d, J = 8.6 Hz, 4H), 5.76 (s, IH), 3.72 (s, 3H).

The synthetic route of 3469-00-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METHYLGENE INC.; WO2008/122115; (2008); A1;,
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