Esters-buliding-blocks

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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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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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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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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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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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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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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These common heterocyclic compound, 4341-76-8, name is Ethyl 2-butynoate, 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. Formula: C6H8O2

Compound A (ethyl 2-butynoate, 1.12 g, 10 mmol) was dissolved in tetrahydrofuran.Add N,O-dimethylhydroxylamine hydrochloride (1.94 g, 20 mmol),Cool to -40 C,Isopropylmagnesium chloride (2M/L, 15 mL, 30 mmol) was added and reacted for 1 h.The reaction was completed, quenched with water, ethyl acetate (200 mL¡Á3), and brine (100 mL¡Á6)Concentrated under reduced pressure and purified by silica gel column chromatographyCompound B (colorless oil, 1.15 g, 91%).

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

Reference:
Patent; Lanzhou University; Tu Yongqiang; Zhang Qing; (20 pag.)CN109666030; (2019); A;,
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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 59833-69-1 as follows. Product Details of 59833-69-1

General procedure: To a stirred solution of 35c (781 mg, 3.9 mmol) and pyridine (0.95 mL, 11.7 mmol) in CH2Cl2 (10 mL) was added a solution of 34a (1.3 g, 3.9 mmol) in CH2Cl2 (10 mL). After stirring overnight at room temperature, the reaction mixture was quenched with water and extracted with EtOAc (¡Á2). The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to yield methyl ester (1.3 g, 63% in 2 steps) as a pale yellow amorphous powder.

According to the analysis of related databases, 59833-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iwahashi, Maki; Naganawa, Atsushi; Kinoshita, Atsushi; Shimabukuro, Atsushi; Nishiyama, Toshihiko; Ogawa, Seiji; Matsunaga, Yoko; Tsukamoto, Kohki; Okada, Yutaka; Matsumoto, Ryoji; Nambu, Fumio; Oumi, Rie; Odagaki, Yoshihiko; Katagi, Jun; Yano, Koji; Tani, Kousuke; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; 22; (2011); p. 6935 – 6948;,
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Adding a certain compound to certain chemical reactions, such as: 4891-38-7, name is Methyl Phenylpropiolate, 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 4891-38-7, COA of Formula: C10H8O2

General procedure: To the mixture of terminal alkyne (1mmol), water (2.0 equiv), and acetic acid (2 mL), silver tetrafluoroborate (5 mol%) was added. The mixture was stirred at 110C for 10 h. Water (10 mL) was added and the solution was extracted with ethyl acetate (3¡Á8 mL), the combined extract was dried with anhydrous MgSO4. The solvent was removed and the crude product was separated by column chromatography to give the pure sample.

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

Reference:
Article; Chen, Zheng-Wang; Ye, Dong-Nai; Qian, Yi-Ping; Ye, Min; Liu, Liang-Xian; Tetrahedron; vol. 69; 30; (2013); p. 6116 – 6120;,
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