Esters-buliding-blocks

Application of 14062-25-0, 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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of ester (20 mmol, 1.0 equiv) in toluene (40 mL) was addedparaformaldehyde (1.80 g, 60 mmol, 3.0 equiv), K2CO3 (8.29 g, 60 mmol, 3.0 equiv),n-Bu4NI (370.0 mg, 1.0 mmol, 0.05 equiv). The reaction mixture was heated to 60 Covernight. After the finish of reaction monitored by TLC, the reaction was cooled toroom temperature, water was added and the aqueous layer was extracted with Et2O(40 mL ¡Á 3). The combined organic layer was dried over anhydrous Na2SO4,concentrated in vacuo. The resulting residue was purified by column chromatographyto give the corresponding acrylate intermediate as a colorless oil. Then, a solution ofsubstituted amine (20 mmol, 2.0 equiv)in THF (13.0 mL) at 0C was added a solutionof corresponding acrylate (10 mmol, 1.0 equiv) in THF (7.0 mL) via addition funnel.The reaction mixture was allowed to warm to ambient temperature then stirred atroom temperature for 24h, and concentrated under vacuum. The resulting residue waspurified by column chromatography to give the corresponding intermediate as a oil.Then to a solution of the oil in dichloromethane (20.0 mL) were added di-tert-butyldicarbonate (2.40 g, 11 mmol) and DMAP (122.0 mg, 1 mmol), and the mixture wasstirred at room temperature for 24h. Saturated aq. NH4Cl was added to the mixtureand the resulting mixture was extracted with dichloromethane. The combined organiclayer was washed with brine, dried over Na2SO4, filtered and evaporated in vacuo.The resulting residue was purified by column chromatography to give thecorresponding intermediate as a colorless oil. Then to a solution of the resulting oil inTHF/H2O (5 mL/5 mL) was added LiOH (1.20 g, 50 mmol, 5 equiv). The reactionmixture was heated at 60 C overnight. After cooling to room temperature, thereaction was acidified using aqueous HCl (6 M), and the aqueous layer was extractedwith Et2O (20 mL ¡Á 3). The combined organic layer was washed with water and brine,dried over Na2SO4, and concentrated in vacuo to give the resulting product 4a-j as acolorless crystal, using for the next step without further purification.

The synthetic route of Ethyl 2-(4-bromophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Li; He, Gu; Pan, Zhaoping; Wu, Fengbo; Yu, Meng; Zeng, Minghui; European Journal of Medicinal Chemistry; vol. 189; (2020);,
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Related Products of 1000342-11-9, The chemical industry reduces the impact on the environment during synthesis 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, I believe this compound will play a more active role in future production and life.

Step 1 : Synthesis of methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl) amino)cyclohexyl)-amino)-2-methylbenzoate: [0671] To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (860 g, 3.53 mol) and tert-butyl (4-oxocyclohexyl)carbamate (904.6 g, 4.24 mol) in dichloroethane (1 L), acetic acid (1274 g, 21.23 mol) was added and reaction was stirred at room temperature for 30 minutes. Then sodium triacetoxyborohydride (2250 g, 10.61 mol) was added at 0 C and reaction was stirred at room temperature for 16 hours. On completion (monitored by TLC), reaction was quenched with aqueous sodium bicarbonate, the organic layer was separated and the aqueous layer was extracted with dichloromethane (1.5 L X 3). The combined organic layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude compound was purified by silica gel column chromatography (100-200 mesh size) eluting with 2, 4, 6 & 8% ethyl acetate in hexane to remove maximum cis isomer. This afforded 945 g of mixture of cis and trans isomers (40:60 by HPLC). The trans isomer was purified by repetitive recrystazlisation with ethyl acetate: hexane (1 :2) to afford 480 g of pure trans isomer as white solid with 99% purity.

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 3-amino-5-bromo-2-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; WO2015/10049; (2015); A1;,
Ester – Wikipedia,
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Application of 1459-96-7, 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 1459-96-7 as follows.

A solution of dimethyl bicyclo[2.2.2]octane-l,4-dicarboxylate (58.0 g, 0.25 mol) in methanol (600 mL) was heated under reflux. To this solution was added a solution of potassium hydroxide (9.8 g, 0.175 mol) in methanol (100 mL) and water (12 mL) over 30 minutes. The reaction mixture was refluxed for 24 h. The solvent was then removed and the residue was diluted with water. The aqueous solution was extracted with ethyl acetate (2 x200 mL) to recover starting material (22.0 g), and the aqueous layer was acidified to pH 3 by addition of hydrochloric acid. A precipitate was formed and extracted with ethyl acetate (3 x 300 mL). The combined extracted were washed with brine, dried over sodium sulfate and concentrated to give the titled product (30.0 g, 0.14 mol, 55 % yield).1H NMR(400 MHz, CDCI3) delta ppm 3.65 (s, 3H), 1.81 (s. 12H); MS (ESI) m/z 211.3 [M-H]”.

According to the analysis of related databases, 1459-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, 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 653-92-9, Safety of Methyl 2-bromo-4-fluorobenzoate

Under a nitrogen atmosphere, a solution of compound 46 (11 g, 47.30 mmol) in 210 mL of toluene was added to 12 mL of water, K3PO4 (20 g, 94.59 mmol) and ethylboronic acid (7 g, 94.59 mmol), followed by the addition of Pd(OAc)2 (149 mg, 0.66 mmol). The mixture was heated to 100C, reacted for 3 hours, and then cooled to room temperature. After filteration, the filter cake was washed with ethyl acetate, and the organic phase was collected and purified by column to obtain a total of 8.3 g of the title compound 47 with a yield of 96.6%.

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; Shenzhen Targetrx, Inc.; WANG, Yihan; LI, Huanyin; (30 pag.)EP3415518; (2018); A1;,
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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. 6065-82-3, name is Ethyl diethoxyacetate, A new synthetic method of this compound is introduced below., name: Ethyl diethoxyacetate

General procedure: A mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.

The synthetic route of 6065-82-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Adib, Mehdi; Saeedi, Sara; Soheilizad, Mehdi; Bayanati, Maryam; Tajbakhsh, Mahmood; Amanlou, Massoud; Journal of Chemical Research; vol. 40; 5; (2016); p. 314 – 317;,
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Adding a certain compound to certain chemical reactions, such as: 39520-24-6, name is Dimethyl 2-isobutylmalonate, 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 39520-24-6, category: esters-buliding-blocks

Taken 500mL four-necked flask was added 18.75g isobutyl-butyl malonate, 18.01g1,2,2,6,6- pentamethyl-piperidinol, 180g xylene, fitted with a reflux condenser, a thermometer, a stirrer and nitrogen, with stirring turn, was heated to 120 deg.] C, was added after 0.5h 0.48g dioctyltin oxide (first catalyst), the reaction continued at reflux for 6h, thin layer chromatography analysis showed that only the end of a significant point, transesterification . A flask was supplemented with 20g of xylene, and adding 26.15g2,6- butylated (dimethylaminomethyl) phenol (tradename antioxidant 703), and 0.41g lithium amide (second catalyst), raising the temperature to 145 deg.] C, the reaction was refluxed for 8h, TLC analysis showed that only a clear point, substitution reaction. After the heating was stopped and cooled to room temperature, the reaction mixture was added 3.5g of acetic acid, stirred for 30min, then the reaction solution was filtered dioctyltin oxide and lithium amide, washed 3 times with 70 water, water per 250ml, taken after the liquid separation the organic layer was recovered and the xylene distilled to give a tan solid which was recrystallized from ethanol and the crystals were washed, and dried to give 59.94g of light yellow powder, i.e., containing both a hindered phenol and a hindered amine structure weathering anti-aging agent. Product yield was 85.7% by HPLC analysis of purity of 94.15%.

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

Reference:
Patent; South China University of Technology; Rookie chemical (Yantai) Co., Ltd.; Cai, Zhiqi; Pi, Peng; Wenxiu, Fang; Lu, Yuan; (10 pag.)CN105294543; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 18469-52-8,Some common heterocyclic compound, 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, molecular formula is C9H11NO2, 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 2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid (1.0 equiv) in DMF was added HOBT (1.2 equiv) and EDCI (1.2 equiv), and the mixture was stirred for thirty minutes at room temperature. Triethylamine and corresponding 5a-5e was added, and then reaction was stirred for 8 h at room temperature. Then it was quenched by H2O. The mixture was washed with brine and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by chromatography on a silica gel chromatography (petroleum ether/ethyl acetate = 1:1 to 1:20) to give corresponding products 6a-6e (yield 43%-62%) as white 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 4-(aminomethyl)benzoate, its application will become more common.

Reference:
Article; Liao, Chenzhong; Tian, Yongbin; Xie, Zhouling; Bioorganic and medicinal chemistry letters; (2020);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 625-56-9, name is Chloromethyl acetate, molecular formula is C3H5ClO2, 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. Application In Synthesis of Chloromethyl acetate

Reference Example 15 A mixture of 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1,2,3-triazol-1-yl)phenyl]-2-imidazolidinone (0.30 g) and chloromethyl acetate (1.35 g) was stirred for 24 hours at 100 C. The reaction mixture was concentrated under reduced pressure. The residue was subjected to ODS column chromatography (eluent: methanol/water=3/2) to give 4-acetoxymethyl-1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-1,2,3-triazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-1H-1,2,4-triazolium chloride (Compound 3, 45 mg) as a white powder. 1H-NMR(d6-DSMO) delta: 0.97(3H,d,J=7 Hz), 2.08(3H,s), 3.61-4.08(4H,m), 4.65-4.75(1H,m), 4.86(1H,d,J=14 Hz), 5.11(1H,d,J=14 Hz), 6.07-6.20(2H,m), 6.69(1H,s), 6.96-7.05(1H,m), 7.25-7.36(2H,m), 7.82-7.95(5H,m), 8.78(1H,s), 9.06(1H,s), 10.46(1H,s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 625-56-9, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6583164; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 3618-04-0, 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Tert-butyl(chloro)diphenylsilane (18 ml, 68 mmol, GAS No 58479-61 -1) was added drop wise to a mixture of ethyl 4-hydroxycyclohexanecarboxylate (9.4 ml, 57 mmol, GAS No 17159-80-7), 1H-imidazole (9.68 g, 142 mmol, GAS No 16681 -56-4) and N,N-dimethylpyridin-4-amine (348 mg, 2.85 mmol, GAS No 1122-58-3) in DMF (81 ml), and the mixture was stirred at roomtemperature for 24 h. For work-up, the mixture was poured into water, extracted with ethyl acetate (3x) and the combined organic phases were washed until pH=7 as reached. The organic phase was dried over sodium sulfate and was concentrated under reduced pressure. The residue was purified by flash chromatography (340 g SNAP cartridge, hexane/ethyl acetate gradient, 5% -> 30% ethyl acetate) to give the title compound (21 g).

The synthetic route of trans-Ethyl 4-hydroxycyclohexanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; WAGNER, Sarah; SUeLZLE, Detlev; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; (232 pag.)WO2018/78009; (2018); A1;,
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Reference of 816-27-3, These common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, 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) 5-Benzyl-1H-[1,2,4]triazole-3-carboxylic acid butyl ester Ethyl-2-ethoxy-2-iminoacetate (1.318 g, 9.08 mmol) and phenyl acetic acid hydrazide (1.364 g, 9.08 mmol) were mixed together in ethanol (20 ml) and stirred at 80 C. for 1 h. Ethanol was evaporated. The residue was dissolved in n-butanol (20 ml). The reaction mixture was stirred at 150 C. for 20 h, then solvents were evaporated. The residue was suspended in acetonitrile and the precipitate was filtered off. The filtrate was purified by prep. HPLC (column: Interchrom C18 ODB, 10 um, 250*28 mm, 23 C.; A: water+0.1% HCOOH, B: ORG+0.1% HCOOH [ORG=methanol/acetonitrile 4:1]; gradient 20% B 2.5 min, 20-100% B in 35 min, 100% B for 2.5 min) to give the title compound. UPLC-MS (method F) Rt=0.85 min, [M+H]+=260.3; HPLC (method G) Rt=1.861 min.

Statistics shows that Ethyl 2-ethoxy-2-iminoacetate is playing an increasingly important role. we look forward to future research findings about 816-27-3.

Reference:
Patent; NOVARTIS AG; US2012/35168; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics