Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 19064-14-3, name is Ethyl 2,6-difluorobenzoate, 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 19064-14-3, SDS of cas: 19064-14-3

A. Ethyl-2-fluoro-6[(3,4-methylenedioxy)phenoxy]benzene-carboxylate Sesamol (3,4-methylenedioxyphenol; 423 mg, 3.0 mmol) was added as a solution in THF (1.0 ml) to a suspension of mineral oil free-sodium hydride (72 mg, 3.0 mmol) in THF (0.5 ml) under water cooling. The mixture was stirred at 25 C. for 20 minutes. The solvent was evaporated at 40 C. under reduced pressure. A solution of ethyl-2,6-difluorobenzene-carboxylate (EXAMPLE 1C; 373 mg, 2.0 mmol) in DMSO (0.5 ml) was added to a solution of the solid prepared above in DMSO (1.0 ml). The brownish solution was heated at 80 C. for 2 hours. The solvent was evaporated, the solid filtered, washed with water several times and dried. The crude product was purified by flash column chromatography on silica gel using 3-15% ethyl acetate in hexane to give 371 mg of the product (61% yield) as a light yellow oil and unreacted sesamol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2,6-difluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Texas Biotechnology Corporation; US5977117; (1999); A;,
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Synthetic Route of 5445-17-0, The chemical industry reduces the impact on the environment during synthesis 5445-17-0, name is Methyl 2-bromopropanoate, I believe this compound will play a more active role in future production and life.

General procedure: In a round-bottomed flask, activated iron dust (168 mg,3 mmol) was added to a solution of alpha-bromo carbonyl compounds (1.0 mmol) and diaryl disulfides (0.5 mmol) in DMF (3.0mL). The reaction mixture was stirred at 90C under N2 atmosphere for 15 h. Then ethyl acetate (20 mL) was added, stirred, and filtered. To filter liquor, the water (15 mL) was added and the mixture was extracted with ethyl acetate (15 mL × 3). The combined organic phase was washed with water (20 mL × 2), dried over anhydrous Na2SO4 , and concentrated under vacuum. The crude product was purified by column chromatography on silica gel (petroleum ether /ethyl acetate = 30:1).

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

Reference:
Article; He, Yun-Hua; Li, Ning-Bo; Chen, Jin-Yang; Qiu, Ren-Hua; Wang, Xie; Xu, Xin-Hua; Synthetic Communications; vol. 45; 15; (2015); p. 1817 – 1822;,
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Some common heterocyclic compound, 105-53-3, name is Diethyl malonate, molecular formula is C7H12O4, 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. category: esters-buliding-blocks

To a sodium ethoxide-ethanol solution, which was prepared by slowly addition sodium (8.625 g, 375 mmol) into ethanol (600 mL) in small pieces, was added diethyl malonate 283A (30 g, 187.5 mmol) at room temperature and stirred at room temperature for 20 minutes. To the solution was added 1,5-dibromopentane (45.29 g, 196.9 mmol) and stirred at reflux for 16 hours. The mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate (200 mL), washed with water (80 mL) and brine (50 mL x 2), dried over anhydrous sodium sulfate, filtered, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether from 0% to 10% v/v) to yield Compound 283B. LC-MS (ESI) m/z: 229 [M+H] ?H-NMR (CDC13, 400 IVII{z): (5(ppm) 1.25 (t, J 7.2 Hz, 6H), 1.40-1.46 (m, 2H), 1.50-1.55 (m, 4H), 1.96-1.99 (m, 4H), 4.18 (q, J= 7.2 Hz, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 105-53-3, its application will become more common.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
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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 369-26-6 as follows. name: Methyl 3-amino-4-fluorobenzoate

Methyl 3-amino-4-fluorobenzoate (2 g, 13 mmol) and pyridine (2.1 g, 76.4 mmol) were suspended in DCM (25 mL), and to the stirring solution was slowly added 2-trifluoromethyl- benzenesulfonyl chloride (3.24 g, 13 mmol) at room temperature. After stirring for 2 h, the reaction mixture was washed with water and then extracted with DCM. The combined organic layers were dried over Na2SOzI, filtered, and concentrated in vacuo. The crude residue was suspended in water (30 mL) followed by slow addition of NaOH (1.1 g, 28 mmol), and the mixture heated at reflux overnight. After cooling to room temperature, the reaction mixture was extracted with DCM. The layers were separated. The aq. layer adjusted to pH 5 with aq. 5N HCl, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford the final product as a solid (4.0 g, 83percent overall). LC-MS (ES) m/z = 364.1 (M+H)+ 1H NMR (400 MHz, DMSO-d6) delta ppm 10.61 (br, 1 H), 10.37 (br, 1 H), 8.78 (m, 1 H), 8.37 (m, 1 H), 8.01 (m, 2 H), 7.71 (m, 2 H), 7.31 (m, 2 H).

According to the analysis of related databases, 369-26-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; LAFRANCE, Louis, Vincent; LEBER, Jack, Dale; LI, Mei; VERMA, Sharad, Kumar; WO2010/126922; (2010); 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. 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, A new synthetic method of this compound is introduced below., Product Details of 23426-63-3

3 g of 5-tert-butyl-2-nitrophenol (15.37 mmol; 1.0 eq) were dissolved in 42 mL of DMF. 15 g of cesium carbonate (46.10 mmol; 3.0 eq) and 5.97 mL of methyl-2-bromo-2-methylpropanoate (46.10 mmol; 3.0 eq) were added and the session medium was stirred at 110 C. for 1 h. After cooling, the medium was diluted in water and the aqueous phase was extracted three times with EtOAc. The organic phases were washed with brine, dried over MgSO4, filtered and concentrated under vacuum, to give 5.11 g of the title compound in the form of a yellow oil. Yld: 100%. 1H NMR (300 MHz, DMSO-d6) deltappm 1.26 (s, 9H) 1.57 (s, 6H) 3.73 (s, 3 H) 6.87 (d, J=1.8 Hz, 1H) 7.23 (dd, J=8.5, 1.8 Hz, 1H) (d, J=8.5 Hz, 1H). LC-MS: m/z (M+H)+: 296.

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; INVENTIVA; BOUBIA, Benaissa; MASSARDIER, Christine; GUILLIER, Fabrice; POUPARDIN, Olivia; TALLANDIER, Mireille; AMAUDRUT, Jerome; BONDOUX, Michel; FEENSTRA, Roelof Williem; VAN DONGEN, Maria Johana Petronella; (207 pag.)US2017/66717; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 10601-80-6, name is Ethyl 3,3-diethoxypropionate, 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 10601-80-6, Application In Synthesis of Ethyl 3,3-diethoxypropionate

To a 500 ml reaction flask was added 100 g of tetrahydrofuran, 10.0 g (0. 1 mol) of 3-acetoxypropylene,41. 8 g (0.22 mol) of ethyl 3, 3-diethoxypropionate, 5.2 g (30 mmol) of 47% boron trifluoride acetamidine solution,Nitrogen was replaced three times, and the temperature was raised to 60 C for 4 hours (recovery of diethyl ether). After completion of the reaction, the solvent was recovered, cooled to 20 C, and added20 g of water and 60 g of ethyl acetate were added and the layers were extracted with ethyl acetate and extracted three times (20 g each of ethyl acetate)The combined organic phase was dried over 20 g of anhydrous sodium sulfate for 4 hours, filtered and the ethyl acetate was recovered to give 2- ((4R, 6S) -6-acetoxyMethyl-2-ethoxycarbonylmethyl-1,3-dioxan-4-yl) acetate 27. 5 g, 98.9% purity (GC)82. 7%

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; XINFA PHARMACEUTICAL CO LTD; QI, YUXIN; LI, XINFA; LU, QIANGSAN; JU, LIZHU; (15 pag.)CN104163808; (2016); B;,
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Related Products of 383-62-0, These common heterocyclic compound, 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, 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.

Into a 250 ml 3-necked round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed NMP (80 ml). To the above was added KF (6.8 g, 0.12 mol) and CuI (15 g, 0.08 mol). After stirring 5-10 min, XIV-A-95 (11 g, 0.04 mol) and ClF2CCO2Et (18 g, 0.12 mol) were added. The resulting solution was stirred for 6 h while the temperature was maintained at 115-125 C. After cooling, 300 ml CH2Cl2 was added to the reaction system. The organic layer was washed with saturated NaCl solution (80 ml×5) and dried with Na2SO4. After evaporating the solvent, the residue was purified by column chromatography (eluant: PE_EtOAc=10:1) and compound XIV-B-95 was collected (4.65 g, 53.1%) as a yellow solid (m.p.: 38-40 C.)

The synthetic route of 383-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kalypsys, Inc.; US2005/234046; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 145576-28-9, name is Ethyl 4-methylenecyclohexanecarboxylate, 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 145576-28-9, COA of Formula: C10H16O2

General procedure: The alkene (1.16 mmol, 1 equivalent) was dissolved in a vigorously stirred mixture of DCM (7 mL) and acetonitrile (7 mL) under nitrogen. 2,6-Lutidine (0.27 mL, 2.32 mmol, 2 equivalents), water (10.5 mL) and sodium periodate (993 mg, 4.64 mmol, 4 equivalents) were then added sequentially. The reaction concentration with respect to the alkene was 0.047 M in a mixture of 1: 1: 1.5 – DCM: acetonitrile: water. To the resulting mixture a stock solution of ruthenium(III) chloride trihydrate (0.035 M in water) (1.16 mL, 0.04 mmol, 3.5 mol %) was added dropwise via a syringe forming a brown suspension. The reaction was stirred vigorously at 20 C for 1 h (or for the time indicated in the Tables 2 and 3). The reaction was diluted with water (20 mL) then extracted with DCM (3 x 20 mL). The organic extracts were combined then washed with brine (20 mL), passed through a phase separating cartridge and the volatiles were removed under reduced pressure. The resulting residue was purified by flash silica chromatography (EtOAc / heptane) to afford the ketone.

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:
Article; Watson, David W.; Gill, Matthew; Kemmitt, Paul; Lamont, Scott G.; Popescu, Mihai V.; Simpson, Iain; Tetrahedron Letters; vol. 59; 51; (2018); p. 4479 – 4482;,
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Electric Literature of 4630-80-2, 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. 4630-80-2, name is Methyl cyclopentanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Synthesis of methyl 1-methylcyclopentanecarboxylate:To a solution of di-isopropylamine (69 ml) in tetrahydrafuran (100 ml), n- BuLi (166 ml) in hexane was added at 0 C and the reaction mixture was allowed to stir at same temperature for about 10-15 minutes. The reaction mixture was stirred at room temperature for about 45 minutes. Methyl cyclopentanecarboxylate (25 g) in tetrahydrafuran (200 ml) was added drop-wise at -78 C to above reaction mixture. The reaction mixture was stirred at same temperature for about 2 hours and then methyl iodide was added drop-wise. The reaction was maintained at -78C for an hour and allowed to attain room temperature. The reaction mixture was stirred overnight at room temperature and quenched at 0 C with saturated aq. NH4C1 solution and the compound was extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over anhydrous Na2S04 and concentrated. Crude product was directly used for the next step. 1H NMR (CDC13, 300 MHz): 3.66 (s, 3H), 2.10- 2.03 (m, 2H), 1.69- 1.64 (m, 4H), 1.50- 1.42 (m, 2H), 1.23 (s, 3H).

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

Reference:
Patent; HETERO RESEARCH FOUNDATION; PARTHASARADHI REDDY, Bandi; MANOHAR SHARMA, Vedula; RATHNAKAR REDDY, Kura; VL SUBRAHMANYAM, Lanka; SUDHAKAR, Neela; WO2012/25857; (2012); A1;,
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Related Products of 10601-80-6, 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 10601-80-6 as follows.

Tin (II) chloride dihydrate (9.026 g, 40.0 mmol) was added to a solution of 4-bromo-2-nitrobenzaldehyde (2.3 g, 10.0 mmol) and EtOH (40 ml) followed by 3,3-diethoxypropionic acid ethyl ester (4.75 g, 25.0 mmol ). The reaction was heated to 90 oc for4 hr upon the cooling, the reaction mixture was concentrated and the residue was dissolved inEtOAc and quenched with sat. NaHC03. The resulting emulsion was filtered through a pad ofcelite and rinsed well with EtOAc. The remaining aqueous layer was extracted with EtOAcand the combined organic layer were washed with brine, dried over Na2S04 andconcentrated. The crude product was purified by silica gel column chromatography with 10-30% ofEtOAc in hexanes to give ethyl 7-bromoquinoline-3-carboxylate (0.6 g, 21.5%). OH(400 MHz; CDCh) 1.47 (3H, t, J= 8.0 Hz), 4.50 (2H, q, J= 8.0 Hz), 7.72 (1H, t, J= 4.0 Hz),7.80 (1H, s), 8.36 (1H,s), 8.82 (1H, s), 9.45 (1H, s). 8c (100 MHz; CDCh) 14.3, 61.7, 123.5,125.4,126.3, 130.2, 131.1, 138.5, 150.2, 151.0, 165.0.

According to the analysis of related databases, 10601-80-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; UNIVERSITY OF KANSAS; HE, John Cijiang; LIU, Ruijie; DAS, Bhaskar; XIAO, Wenzhen; LI, Zhengzhe; LEE, Kyung; (32 pag.)WO2018/129274; (2018); A1;,
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