Month: July 2021

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. 19063-55-9, name is 6-Bromochromen-2-one, A new synthetic method of this compound is introduced below., Quality Control of 6-Bromochromen-2-one

(1) Weigh 5.2 g of DL-malic acid (38.78 mmol) in a SCHLENK reaction tube.10 g of m-bromophenol (58.17 mmol) was added under N2 atmosphere.13mL of 98% concentrated sulfuric acid was added dropwise with stirring in an ice bath.The reaction was stirred at 120 C for 6 h. After the reaction, cool to room temperature.The reaction solution was slowly dropped into a stirred saturated saline solution, and filtered to give a solid.It was redissolved in dichloromethane, washed with water three times, and the organic phase was dried over anhydrous sodium sulfate.concentrate. Separated and purified by silica gel column chromatography.The mobile phase was petroleum ether/dichloromethane = 3/2. Finally, both Br-C5 and Br-C7 were obtained as white solids, respectively 1.60 g, 5.66 g.

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; Xi’an Jiaotong University; Zhou Guijiang; Feng Zhao; Yang Xiaolong; (40 pag.)CN109608502; (2019); A;,
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Electric Literature of 18469-52-8, A common heterocyclic compound, 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, molecular formula is C9H11NO2, 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: To a solution of acid 3 (1.25 g, 3.1 mmol), HBTU (1.6 g, 3.7 mmol),and Et3N (10 mL) in 20 mL acetonitrile was added 1.2 equimolaramount of the appropriate amine. The mixture was kept stirring atroom temperature for 5 h. TLC detection found that the reactionwas complete, then the mixture was evaporated under reducedpressure to remove solvent. The residue was taken up saturatedsodium chloride and 1mL 3 N HCl and extracted with ethyl acetate(30 mL x 3), and the combined organic layers were washed twotimes with saturated sodium chloride and 1mL 3 N HCl. Theorganic layers were dried (MgSO4), filtered, and solvent wasremoved under reduced pressure at 40 C to give the crude product,which was purified by column chromatography to produce thecorresponding intermediate, 4 and 7.

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; Jia, Ruifang; Zhang, Jian; Ai, Wei; Ding, Xiao; Desta, Samuel; Sun, Lin; Sun, Zhuosen; Ma, Xiuli; Li, Zhong; Wang, Defeng; Huang, Bing; Zhan, Peng; Liu, Xinyong; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 64 – 80;,
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Reference of 13078-21-2, These common heterocyclic compound, 13078-21-2, name is Ethyl 2-(2-methoxyphenoxy)acetate, 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 mixture of phenols (0.3 mmol), acetone (10 ml), dimethylformamide(10 ml), ethyl chloroacetate (2.5 ml, 0.26 mmol), potassiumcarbonate (2 g) and potassium iodide (0.15 g) was heated at75 C for 12 h. Afterwards, the solid was filtered and the solventof the filtrate was removed in vacuo. The colorless liquid (4a-f)obtained was dissolved in ethanol (20 ml). A solution of potassiumhydroxide (7.2%, 5 ml) was added and stirred at room temperaturefor 1.5 h. The mixture was poured into hydrochloric acid (1 mol/L)and a white precipitate was formed. Purification by recrystallizationfrom methanol afforded the corresponding aryloxyl acid (5a-f)

The synthetic route of 13078-21-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Wenbin; He, Yi; Xu, Pei; You, Qidong; Xiao, Hong; Xiang, Hua; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4428 – 4433;,
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Related Products of 2901-13-5, These common heterocyclic compound, 2901-13-5, name is Ethyl 2-methyl-2-phenylpropanoate, 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.

A solution – o’f 1 g- 2-methyl-2-phenyl-propionic acid ethyl ester in a mixture of 14 ml ‘sulfuric acid and 1 ml nitric acid was stirred at room temperature for 4 hours. The mixture was added to ice water and extracted with ethyl acetate. The organic layer wa’s washed with a satured aqueous solution of sodium hydrogen carbonate and dried over – anhydrous sodium sulfate. Filtration and concentration of the solvent under reduced pressure yielded a yellow solid;. The residue was purified- by, .flash chromatography on silica gel with a n-heptane/ dichloro-methane gradient. The fractions containing the product were combined and evaporated . to yield a yellow solid. Yield: 560 -mg.’- ‘ ‘ ‘M+H+. measured = ? ? ? ?1H-NMR’ (400 MHz, DMSO/TMS.)’1: ‘d = 8.69 (d, 1H) ; 8.5.3. (dd,’1H-); 8.10 ? (d, ‘1H) ; -”4 I 02 (q,–2H); 1.65 (s, 6H) ; ,1> 12 (t,

Statistics shows that Ethyl 2-methyl-2-phenylpropanoate is playing an increasingly important role. we look forward to future research findings about 2901-13-5.

Reference:
Patent; AVENTIS PHARMA S.A.; WO2006/10642; (2006); A1;,
Ester – Wikipedia,
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Reference of 25542-62-5, A common heterocyclic compound, 25542-62-5, name is Ethyl 6-bromohexanoate, molecular formula is C8H15BrO2, 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.

EXAMPLE 26; ethyl 6-{5-cyarto-1H-indol-1-yi)hexanoate; [00233] Cyanoi?dole ( 500 mg, 3.52 mmol ) was added to a suspension of sodium hydride (1.1 eq. 148 mg of 60% dispersion m mineral oii) in dimethylformamide and the reaction was stirred for 10 min. Then ethyl 6-bromohexanoate (1 5 eq, 1.18 g, 5.28 mmol ) was added dropwsse. The reaction was stirred at ambient temperature for 5 hours. Then water (8 :1) added and this was extracted with ethyl acetate. The ethyl acetate solution was concentrated in vacio and the residue was purified by silica gel column using ethyl acetate/ hexane as an eluting solvent to afford ethyl 6-{5-cyano~1 H-indol-1- yl)bexanoate (850 mg, 85% yield). 1H NMR {300 MHz, d6-DMSO): delta 8.057(d, J=1.172 Hz1 1H), 7.65(d. J=8.793 Hz. 1H), 7.6(d, J=2.93 Hz, 1H), 7.5(dd, J=1.759Hz, 8.79Hz, 1H), 6.6(d, J=3,5 Hz, 1H), 4.2(t, J=7.03 Hz, 2H), 3.98{q, J=7.034 Hz, 2H), 2.2(t, J=7.3, 2H)1 1.72(pent, J=7.62 Hz, 2H), 1.5(pe?t, J=7.62 Hz, 2H), 1.2( m, 2H)1 1.1(1, J=7.034 Hz, 3H).

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; NUADA, LLC; WO2007/134169; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 85953-29-3, 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. 85953-29-3, name is Methyl 2-chloro-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1 : tert-butyl 4-((l-(3-chloro-4-(methoxycarbonyl)phenyl)piperidin-4-yl)methyl)piperidine- 1-carboxylate A mixture of methyl 2-chloro-4-fluorobenzoate (367 mg, 1.95 mmol), tert-butyl 4-(piperidin-4- y lmethyl)piperi dine- 1-carboxy late (500 mg, 1.77 mmol), and CS2CO3 (1269 mg, 3.89 mmol) in DMSO (8.8 ml) was degassed by bubbling with N2 and heated at 120C for lh under microwave condition. The mixture was diluted with EtOAc-H20, and the aq. layer was extracted with EtOAc (3x). The combined organic fractions were dried over Na2SC>4, filtered and the solvent was evaporated under reduced pressure. The reaction mixture was purified by ISCO column chromatography (silica gel ISCO 40 g prepacked column, eluting with 0-100% EtOAc/Hexane) to give the title compound (578 mg). LCMS m/z (M+H): Calc’d 451.2, found 451.4.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; RUDD, Michael, T.; BENNETT, David Jonathan; WAI, Jenny; MENG, Zhaoyang; (257 pag.)WO2017/95758; (2017); A1;,
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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 4891-38-7 as follows. Application In Synthesis of Methyl Phenylpropiolate

General procedure: Steroidal/nonsteroidal bromo vinyl aldehyde (0.5 mmol), alkyne (0.5 mmol), benzyl amine (0.5 mmol), Pd(OAc)2 (5 mol%), PPh3 (10 mol%), Na2CO3 (1.5 mmol) and neutral alumina (200 mg) were mixed intimately and the mixture was irradiated in a closed vessel in a Synthos 3000 microwave reactor at 600 Watt (140 C and 12 bar) for 10 min. After 10 min ethylacetate (30 mL) was added to the reaction mixture and it was filtered through whatman filter paper. The residue obtained after removal of ethylacetate layer was purified by silica gel column chromatography using EtOAc/hexane as the eluent to afford the pyridine derivative. The alumina on the filter paper was then dried in vacuo and can be used again for another two times in place of Pd(OAc)2 without substantial loss of the yield of the product.

According to the analysis of related databases, 4891-38-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shekarrao, Kommuri; Nath, Dipankar; Kaishap, Partha Pratim; Gogoi, Sanjib; Boruah, Romesh C.; Steroids; vol. 78; 11; (2013); p. 1126 – 1133;,
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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. 18830-44-9, name is Methyl 3,3,3-trifluoropropanoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

28.1. methyl 2-benzyl-4,4,4-trifluoro-3,3-dihydroxybutanoate To a solution of 675 mg (29.4 mmol) of sodium in 15 mL of anhydrous MeOH, under argon, are added dropwise 3.73 mL (29.4 mmol) of methyl 3,3,3-trifluoropropanoate. After stirring for 30 minutes at room temperature, 3.5 mL of benzyl bromide are added and the medium is heated for 12 hours at 70 C. The reaction mixture is then concentrated under reduced pressure. The residue obtained is taken up in 100 mL of EtOAc, washed with 50 mL of brine, dried over Na2SO4, filtered and concentrated under reduced pressure. After purification by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc mixture (85/15), 3.4 g of methyl 2-benzyl-4,4,4-trifluoro-3,3-dihydroxybutanoate are obtained in the form of an oil, which is used without further purification in the following step. Yield=37%.

The synthetic route of 18830-44-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; US2011/294788; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 454-31-9, The chemical industry reduces the impact on the environment during synthesis 454-31-9, name is Ethyl 2,2-difluoroacetate, I believe this compound will play a more active role in future production and life.

Into a 250-mL 3-neck round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 1,4-dibromobenzene (12.0 g, 50.8 mmol, 1.0 equiv) in THF (150.0 mL) at -78 C. Then n-butyllithium solution (1 M in hexane, 60.9 mL, 60.9 mmol, 1.2 equiv) was added at -78 C. The resulting mixture was stirred for 30 minutes at -78 C., and then ethyl 2,2-difluoroacetate (12.6 g, 101.5 mmol, 2.0 equiv) was added slowly at -78 C. The cooling bath was removed, and the resulting mixture was stirred for an additional 1 hour at room temperature. The reaction was then quenched by the addition of 50 mL water. The resulting mixture was extracted with ethyl acetate (250 mL*3), and the organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1:10). This resulted in 7.6 g (64%) of 1-(4-bromophenyl)-2,2-difluoroethan-1-one as a light yellow semi-solid.

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 2,2-difluoroacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Arvinas Operations, Inc.; Genentech, Inc.; Crew, Andrew P.; Wang, Jing; Berlin, Michael; Dragovich, Peter; Chen, Huifen; Staben, Leanna; US2019/300521; (2019); A1;,
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Reference of 23426-63-3,Some common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, molecular formula is C5H9BrO2, 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.

A mixture of 3-(3,3-dimethyl-6-trifiuoromethyl-l,2,3,4-tetrahydro-quinolin-2-yl)- phenylamine (1.5 g, 4.7 mmol), 2-bromo-2-methyl-propionic acid methyl ester (2.55 g, 14.1 mmol) and potassium carbonate (3.24 g, 23.5 mmol) in N, N-dimethylformamide (12 mL) was stirred at 25C for 5 d. Then the reaction mixture was extracted with ethyl acetate (2 x 100 mL), washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification on flash silica gel chromatography (silica gel from QingDao, 200- 300 mesh, glass column from Shanghai SD company)(30% ethyl acetate/hexanes) to afford 2-[3-(3,3-dimethyl-6-trifiuoromethyl-l,2,3,4-tetrahydro-quinolin-2-yl)-phenylamino] -2- methyl-propionic acid methyl ester (400 mg, 20%) as a brown oil. LC/MS m/e calcd for C23H27F3N2O2 (M+H)+: 421.48, observed: 421.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-bromo-2-methylpropanoate, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Li; FENG, Lichun; HUANG, Mengwei; LIU, Yongfu; WU, Guolong; WU, Jim, Zhen; ZHOU, Mingwei; WO2011/128251; (2011); A1;,
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