Category: esters-buliding-blocks

Related Products of 120-61-6,Some common heterocyclic compound, 120-61-6, name is Dimethyl terephthalate, molecular formula is C10H10O4, 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 of 4.01 g of dimethyl terephthalate in methanol and 42 g of a methanol solution of dimethyl terephthalate was prepared.0.4003 g of the activated-passivated nickel-containing catalyst and 0.8005 g of the copper-based catalyst were added and hydrogenation reaction was carried out at 200 C. under a hydrogen pressure of 4 MPa and stirring at 700 r/min for 4 h. The temperature was then raised to 240C, the hydrogen pressure was adjusted to 8 MPa, and the reaction was carried out for 4 hours while stirring at 700 r/min. After the reaction was cooled down to room temperature overnight, the catalyst was separated by centrifugation, filtration, and the solution was distilled to obtain 1,4-cyclohexanedimethanol product after purification. The yield was 92%.

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

Reference:
Patent; Shandong Yuhuang Chemical Co., Ltd.; Yuan Benfu; Pang Fei; Guo Chunping; Xu Longkun; Wang Rongguang; Wang Hui; Wang Zhongya; Hou Hongxia; Wang Jianwei; Wang Shengwei; (6 pag.)CN107805183; (2018); A;,
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Synthetic Route of 22223-49-0, 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. 22223-49-0 name is Methyl 2-amino-3-methylbenzoate, 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: CuCl (1.50 mg, 0.0150 mmol), DPEPhos (8.10 mg, 0.0150 mmol) and KOt-Bu (1.70 mg,0.0150 mmol) were added to a 8 mL vial charged with a magnetic bar. The vial was sealedwith a cap (phenolic open top cap with gray PTFE/silicone) and purged by N2 gas for 5 min.Toluene (0.8 mL) and methyl 2-aminobenzoate (1a) (46.6 L, 0.360 mmol) were added to themixture, which was allowed for 10 min. And then a solution of phenyl vinyl sulfone (2) (50.5mg, 0.300 mmol) in toluene (0.7 mL) was added to the reaction solution. After stirring atroom temperature for 5 h, THF (5 mL) was added and the reaction was allowed to cool to 0C (ice bath). After addition of KOt-Bu (101 mg, 0.900 mmol), the resulting solution wasallowed to stir for further 1 h at 0 C. After that time, the reaction was quenched with asaturated aqueous solution of NH4Cl (1 mL) and NaHCO3 (2 mL) and washed with EtOAc (7x 3 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated invacuo. The crude product was purified by silica gel column chromatography (CH2Cl2/EtOAc,8:1) to afford the desired product 4a (76.8 mg, 0.267 mmol, 89% yield) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Article; Kang, Seongil; Yoon, Hongju; Lee, Yunmi; Chemistry Letters; vol. 45; 12; (2016); p. 1356 – 1358;,
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193290-19-6, name is Methyl 2-(4-bromo-2-fluorophenyl)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: C9H8BrFO2

Step B: To a solution of intermediate 1 (10.35 g, 0.042 mol) in 210 mL THF at -70 C was added n-BuLi (1.6 M in hexane, 28 mL, 0.045 mol). The mixture was stirred at -70 C for 1 h before a solution of 4-bromo-2-fluorophenyl acetic acid methyl ester (10.55 g, 0.043 mol) in 10 mL THF was added. The reaction mixture was allowed to warm to room temperature and stirred for another Ih. The reaction was quenched with ice water (200 mL), and the product was extracted with CH2Cl2. The extracts were dried over MgSO4, filtered, and concentrated. Column chromatography (2% EtOAc/PE) of the residue afforded the title compound.

The synthetic route of 193290-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2008/51404; (2008); A2;,
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These common heterocyclic compound, 56441-97-5, name is Methyl 4-(benzyloxy)-3-methoxybenzoate, 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. Product Details of 56441-97-5

To a solution of 4-benzyloxy-3-methoxy-benzoic acid methyl ester (7.08 g, 26 mmol) in acetic acid (50 ml), at O0C, was added dropwise nitric acid (7 ml) over 10 minutes. The reaction mixture was warmed to room temperature and then stirred at 60 0C for 1 hour. The reaction mixture was poured into water, extracted with DCM (3×125 ml) and the combined organic extracts were washed with water, saturated aqueous NaHCO3, brine, dried (MgSO4) and concentrated to provide the title compound as a pale yellow solid (7.5 g). LC/MS purity: 95 %, m/z 318 [M+H]+. 1H NMR (300 MHz, CDCI3) delta: 7.55 (1 H, s), 7.53-7.39 (5H, m), 7.11 (1H, s), 5.23 (2H, s), 3.99 (3H1 s), 3.92 (3H, s).

The synthetic route of Methyl 4-(benzyloxy)-3-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHROMA THERAPEUTICS LTD; WO2006/117552; (2006); A1;,
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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. 10602-06-9, name is Methyl 3-ethynylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 10602-06-9

General procedure: CuCl (0.04 mmol), 2,4,6-trimethylpyridine (0.4 mmol), trifluoromethylating reagent 2a (0.24 mmol) and terminal alkynes (0.2 mmol) were added to a Schlenk tube which was equipped with a stirring bar. DMAc (1 mL) was added under argon atmosphere to this tube. After the addition of all materials, the reaction mixture was kept for 24 h at 30 C. After the reaction, ethyl acetate was added. The organic layer was separated, and washed with water. The combined organic extracts were washed with brine, and dried over MgSO4. After evaporation of the solvent, the crude product was purified by chromatography on silica gel to give the product.

According to the analysis of related databases, 10602-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Luo, Dong-Fen; Xu, Jun; Fu, Yao; Guo, Qing-Xiang; Tetrahedron Letters; vol. 53; 22; (2012); p. 2769 – 2772;,
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Synthetic Route of 773134-11-5, A common heterocyclic compound, 773134-11-5, name is Methyl 4-bromo-2,6-difluorobenzoate, molecular formula is C8H5BrF2O2, 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.

Under argon, a microwave vessel was charged with 54 mg(0.22 mmol) of methyl 4-bromo-2,6-difluorobenzoate, 118 mg (1.01 mmol, 4.7 eq.)of tert-butyl carbamate, 4.6 mg (0.02 mmol, 0.1 eq.) of palladium(II) acetate,15 mg (0.026 mmol, 0.13 eq.) of Xantphos, 137 mg (0.42 mmol, 2 eq.) of caesiumcarbonate and 2 ml of 1,4-dioxane. A stream of argon was passed through thesuspension for 2 min. The reaction mixture was heated in the microwave at 140 Cfor 20 min. After filtration through kieselguhr, the filtrate was concentratedunder reduced pressure. The crude product was purified by normal phasechromatography (mobile phase: dichloromethane/methanol 10-50% mixtures). Yield: 37 mg (60% of theory)

The synthetic route of 773134-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; Rurik, Jujane; Hilliswe, Alexander; Strassburke, Yulia; Hidemeyer, Stefan; Smith, Martina Victoria; Schlemmer, Karl-Heinz; Terstigen, Adrian; Buchmuller, Anya; Gerdes, Hirstoph; Schappe, Martina; Kinchel, Tom; Teller, Henryk; Shirok, Hartmut; Klar, Juergen; Jimenez, Nunez Eloisa; (352 pag.)KR2015/137095; (2015); A;,
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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.

Preparation b-1 Methyl 2-(3-cyanophenoxy)-2-methylpropanoate To a solution of 3-cyanophenol (5 mmol) in acetonitrile (20 mL) or any polar, aprotic solvent such as dimethyl sulfoxide, N,N-dimethylformamide, etc) was added methyl 2-bromo-2-methyl-propanoate (1.2 equiv) and cesium carbonate (2 equiv). The resulting was mixture heated at 60 C. for 6 hours and then cooled to ambient temperature. Water (20 mL) was introduced and the mixture extracted with ethyl acetate (3*20 mL). The combined organics were washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and evaporated to dryness to provide the title compound in 75% yield. LRMS: 220 (M+H)+. 1H NMR (CDCl3, 400 MHz): delta 7.30 (1H, t, J=8.0 Hz), 7.23 (1H, dt, J=1.3, 7.6 Hz), 7.05 (1H, dd, J=1.3, 2.3 Hz), 7.01 (1H, ddd, J=2.3, 2.8, 8.3 Hz), 3.73 (3H, s), 1.57 (6H, s).

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; Pfizer Inc; US2005/187266; (2005); A1;,
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Related Products of 394-35-4, A common heterocyclic compound, 394-35-4, name is Methyl 2-fluorobenzoate, molecular formula is C8H7FO2, 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.

3-(tert-Butoxycarbonylamino)piperidine (7.07 g, 35.3 mmol) was dissolved in N,N-dimethylformamide (120 mL). To this solution, potassium carbonate (9.80 g, 70.9 mmol) and methyl 2-fluorobenzoate (5.0 mL, 39.2 mmol) were added and the mixture was stirred at 130¡ãC for 8 hours. Subsequently, the mixture was allowed to cool, diluted with ethyl acetate, and washed sequentially with water and brine. The washed product was dried over sodium sulfate and the solvent was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane: ethyl acetate = 10:1 -> 5:1) gave 2.34 g (20percent) of the desired compound as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 1.46 (9H, s), 1. 55-1. 66 (2H, m), 1. 74-1. 85 (1H, m), 1.86-1.98 (1H, m), 2.84 (1H, t, J = 9.8 Hz), 2.98 (1H, dd, J = 11.6, 5.0 Hz), 3.01-3.10 (2H, m), 3.86-3.92 (1H, m), 3.94 (3H, s), 5.62 (1H, brs), 7.01-7.07 (2H, m), 7.41 (1H, t, J = 8.6 Hz), 7.69 (1H, d, J = 6.1 Hz).

The synthetic route of 394-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYORIN PHARMACEUTICAL CO., LTD.; EP1780210; (2007); 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. 35179-98-7, name is Chloromethyl ethyl carbonate, A new synthetic method of this compound is introduced below., Recommanded Product: 35179-98-7

To a solution of (2S,3S)-3-((2-bromo-5-fluoro-6-(thiophen-2-yl)pyrimidin-4-yl)amino)bicyclo[2.2.2]octane-2-carboxylic acid (2.00 g, 4.69 mmol) in DMF (20 mL) wereadded potassium carbonate (2.02 g, 14.20 mmol) and chloromethyl ethyl carbonate (0.79 g, 5.70mmol), and the mixture was stirred at rt overnight. To the reaction mixture was added water (50mL), and the resulting mixture was extracted with ethyl acetate (50 mL x 3). The combinedorganic layers were washed with saturated brine (100 mL x 3), dried over anhydrous sodiumsulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silicagel column chromatography (PE/EtOAc (v/v) = 511) to give the title compound as a light yellowsolid (0.48 g, 69 % ).MS (ESI, pos. ion) m/z: 527.7 [M+Ht;1H NMR (400 MHz, CDCb) 8 (ppm): 7.84-7.81 (m, 1H), 7.57 (d, J = 5.0 Hz, 1H), 7.20-7.14(m, 1H), 6.02 (d, J = 5.7 Hz, 1H), 5.77 (d, J = 5.6 Hz, 1H), 4.45 (d, J = 5.2 Hz, 1H), 4.24 (q, J =7.1 Hz, 2H), 2.50 (d, J = 5.4 Hz, 1H), 2.03 (d, J = 2.3 Hz, 1H), 1.91 (d, J = 2.4 Hz, 1H), 1.81 (m,1H), 1.72 (m, 4H), 1.65- 1.57 (m, 2H), 1.33 (t, J = 7.1 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; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (303 pag.)WO2018/108125; (2018); A1;,
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6520-83-8, name is Ethyl 2-methoxy-6-methylbenzoate, 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. Recommanded Product: Ethyl 2-methoxy-6-methylbenzoate

Ethyl 3-bromo-6-methoxy-2-methylbenzoate (13-2). To a methylene chloride solution (100 mL) of Ethyl 2-methoxy-6-mefhylbenzoate (13-1, 5 g, 25.8 mmol, TCI Ml 120) was added bromine (1.65 mL, 32.2 mmol, 1.25 equiv) at O 0C. The reaction was stirred at O 0C to 25 0C for 12 h and quenched with sodium thiosulfate solution (5%, 20 mL) and stirred for 20 min. The resulting mixture was extracted with methylene chloride. The combined methylene chloride extracts were dried(Na2SO4) and concentrated to give 7.2 g of 13-2: 1H NMR (400 MHz, CDCl3) delta 7.47 (d, J= 9.2 Hz, 1 H), 6.63 (d, J= 9.2 Hz, 1 H)5 4.38 (q, J= 7.3 Hz, 2 H), 3.78 (s, 3 H), 2.30 (s, 3 H), 1.35 (, J= 7.3 Hz, 3 H).

The synthetic route of 6520-83-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TETRAPHASE PHARMACEUTICALS, INC.; DENG, Yonghong; PLAMONDON, Louis; SUN, Cuixiang; XIAO, Xiao-Yi; ZHOU, Jingye; SUTCLIFFE, Joyce, A.; RONN, Magnus, P.; WO2011/25982; (2011); A2;,
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