Esters-buliding-blocks

Application of 105-53-3, A common heterocyclic compound, 105-53-3, name is Diethyl malonate, molecular formula is C7H12O4, 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: In an atmosphere controlled glovebox, Cu(OTf)2 (398 mg, 1.10 mmol, 2.20 equiv.), arylboroxine (0.330 mmol, 0.670 equiv.), and CsOAc (106 mg, 0.550 mmol, 1.10 equiv.) were added sequentially to a 2 dram vial charged with a stir bar. The sp3-carbon nucleophile (0.500 mmol, 1.00 equiv.) and triethylamine (0.210 mL, 1.50 mmol, 3.00 equiv.) were added as a solution in anhydrous 1,2-DCE (1.20 mL). Additional 1,2-DCE (2¡Á0.5 mL) was used to quantitatively transfer the solution to the reaction mixture. The vial was sealed with a PTFE-lined cap and stirred outside the glovebox at 30 C. Reaction progress was generally monitored by GC-FID using n-dodecane as an internal standard. Unless otherwise noted, reactions were quenched after 36-48 hours, when >95% conversion of sp3-carbon nucleophile was reached. The reaction was quenched with 5 mL of brine and extracted with EtOAc (4¡Á10 mL). The organic layer was then washed with 5 mL brine and dried with Na2SO4, and the solvent was removed by vacuum. The crude residue was purified by flash silica gel chromatography. Note: the order of addition of reagents is important for achieving optimal yields.

The synthetic route of 105-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Governors of the University of Alberta; LUNDGREN, Rylan; MOON, Patrick; (56 pag.)US2018/186721; (2018); A1;,
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These common heterocyclic compound, 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, 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: C5H7BrO2

General procedure: To a 20 mL two-necked round-bottom flask attached with areflux condenser were added V-65 (25 mg, 0.1 mmol) and K2CO3(138 mg, 1.0 mmol), and this flask was purged with argon.Then, 1-nonanal (1a, 71 mg, 0.5 mmol), methyl 2-(bromomethyl)acrylate (2a, 269 mg, 1.5 mmol), and degassedbenzene (5 mL) were added. The mixture was stirred at 60 C for1 h. The reaction mixture was filtered through a short plug ofCelite, and the filtrate was concentrated under reduced pressure.The residue was purified by flash column chromatographyon SiO2 (hexane/EtOAc = 1:0 to 30:1) and preparative HPLC(chloroform) to give methyl 2-methylene-4-oxododecanoate(3b, 101 mg, 84%).

The synthetic route of Methyl 2-(bromomethyl)acrylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kippo, Takashi; Kimura, Yuki; Ueda, Mitsuhiro; Fukuyama, Takahide; Ryu, Ilhyong; Synlett; vol. 28; 14; (2017); p. 1733 – 1737;,
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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. 19063-55-9, name is 6-Bromochromen-2-one, A new synthetic method of this compound is introduced below., Formula: C9H5BrO2

General procedure: Under inert atmosphere (N2), in a 25 mL round bottom flask, Ar3Bi (0.208 mmol; 0.35 eq.), CsF (0.24 g: 1.8 mmol; 3 eq.), PPh3 (0.004 g: 0.018 mmol; 3 mol%), the aryl bromide (0.60 mmol; 1 eq.) was added to DMF (5 mL). The solution was warmed to 90 C prior addition of PEPPSI IPr (0.012 g: 0.018 mmol; 3 mol%). The reaction was monitored by GC/MS to follow the total consumption of the aryl bromide. Cooled to room temperature (RT), the reaction mixture was diluted by addition of diethyl ether (20 mL) and aqueous HCl 6 M (30 mL). After decantation, the aqueous solution was extracted with diethylether (2 * 20 mL). The collected organic phases were then washed with HCl 6 N (2 * 25 mL), water (25 mL) and brine (25 mL) prior drying over MgSO4. After concentration under reduced pressure, the resulting crude product was subjected to purification by column chromatography leading after concentration under reduced pressure to the title compound.

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; Cassirame, Benedicte; Condon, Sylvie; Pichon, Christophe; Journal of Molecular Catalysis A: Chemical; vol. 425; (2016); p. 94 – 102;,
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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. 1214334-90-3, name is Methyl 2-bromo-4-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H6BrF3O2

To a solution of 400 mg (1.413 mmol) 2-bromo-4-trifluoromethyl-benzoic acid methyl ester, 146 mg (1.696 mmol) cyclopropyl boronic acid, 1.21 g (4.946 mmol) tri-potassium phosphate monohydrate, 40.9 mg (0.141 mmol) tricyclohexyl phosphine in 6 ml toluene and 0.3 ml water under nitrogen at room temperature, was added 15.9 mg (0.0707 mmol) palladium acetate. The mixture was stirred in a 100 C. oil bath for 4 hours and overnight at room temperature under nitrogen. The mixture was cooled to room temperature. Water was added and the mixture extracted with ethyl acetate. The organic layer was washed once with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 10%) to provide 0.24 g (71%) of the title compound as a yellow oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1214334-90-3.

Reference:
Patent; Kolczewski, Sabine; Pinard, Emmanuel; Stalder, Henri; US2010/197715; (2010); A1;,
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Related Products of 17100-63-9,Some common heterocyclic compound, 17100-63-9, name is Methyl 4-bromo-3-methoxybenzoate, molecular formula is C9H9BrO3, 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: The methyl benzoate (200-1500 mg), PdCl2(CH3CN)2 (0.02 eq)and SPhos (0.08 eq) were added to a pressure tube. Then, 1,4-dioxane (0.5-3.5 mL) and Et3N (0.5-2 mL) were added under N2 atmosphere, followed by dropwise addition of HBpin (1.5 eq) while stirring under N2 atmosphere. The reaction mixture was heated to 80 C and stirred for 5-20 h. After cooling to rt, the reaction mixturewas filtered through a Celite pad. If further purificationwasperformed, it is specified in each specific example. 4.6.3 Methyl 3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate fx9 The target compound was prepared as described in Section 4.6 , starting with methyl 4-bromo-3-methoxybenzoate (501 mg, 2.05 mmol). The crude oil (600 mg) was used without further purification. 1H NMR spectroscopy confirmed the presence of 54% of the desired product by comparison with the literature [54] . 1H NMR (600 MHz, DMSO-d6) delta: 7.65-7.63 (m, 1H), 7.54-7.52 (m, 1H), 7.44-7.43 (m, 1H), 3.86 (s, 3H), 3.80 (s, 3H), 1.28 (s, 12H).

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-bromo-3-methoxybenzoate, its application will become more common.

Reference:
Article; Bugge, Steffen; Buene, Audun Formo; Jurisch-Yaksi, Nathalie; Moen, Ingri Ullestad; Skj¡ãnsfjell, Ellen Martine; Sundby, Eirik; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 255 – 274;,
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Adding a certain compound to certain chemical reactions, such as: 6914-71-2, name is 1,1-Cyclopropanedicarboxylic acid dimethyl ester, 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 6914-71-2, Application In Synthesis of 1,1-Cyclopropanedicarboxylic acid dimethyl ester

Synthesis of Cyclopropane-1,1-dicarboxylic acid methyl ester KOH (42 mg, 0.75 mmol) was added to a solution cyclopropane-1,1-dicarboxylic acid dimethyl ester (100 mg, 0.63 mmol) in methanol. The resulting mixture was stirred for 4 hours at ambient temperature then concentrated. The residue was diluted with water, acidified with conc. HCl and the product was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford 65 mg (71%) of cyclopropane-1,1-dicarboxylic acid methyl ester.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1-Cyclopropanedicarboxylic acid dimethyl ester, and friends who are interested can also refer to it.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; US2009/239848; (2009); A1;,
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Application of 35179-98-7, These common heterocyclic compound, 35179-98-7, name is Chloromethyl ethyl carbonate, 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.

ELQ-300 (0.85 g, 1.8 mmol), tetrabutylammonium iodide (1.33 g, 3.6 mmol) and potassium carbonate (0.50 g, 3.6 mmol) were dissolved anhydrous dimethylformamide (8 ml) in a flame-dried round bottom flask at 60 C under inert atmosphere. Chloromethyl ethyl carbonate (0.5 g, 3.6 mmol) was added dropwise and the reaction stirred under inert atmosphere at 60 C for two hours, at which point reaction completion was confirmed by thin layer chromatography. After cooling to room temperature, the reaction solvent was removed under reduced pressure and the mixture taken up in water (10 ml) and extracted with dichloromethane (3 x 20 ml). Combined organic layers were washed with brine (10 ml), dried over MgS04, and the dichloromethane evaporated under reduced pressure. The resulting crude product was purified by flash chromatography (EtOAc/DCM) to yield the title compound, ELQ- 331, as a white crystalline solid (560 mg, 54%). 1H NMR (400 MHz, DMSO-d6): delta = 7.98 (s, 1H), 7.57 (s, 1H), 7.44 (m, 4H), 7.21 (m, 4H), 5.76 (s, 2H), 5.35 (s, 2H), 4.03 (s, 3H), 2.44 (s, 3H), 1.11 (t, 3H, J = 7.1 Hz); M.P. (C): 103.5-103.7.

Statistics shows that Chloromethyl ethyl carbonate is playing an increasingly important role. we look forward to future research findings about 35179-98-7.

Reference:
Patent; OREGON HEALTH & SCIENCE UNIVERSITY; THE UNITED STATES GOVERNMENT AS REPRESENTED BY THE DEPARTMENT OF VETERANS AFFAIRS; RISCOE, Michael; NILSEN, Aaron; STICKLES, Allison; MILEY, Galen; WINTER, Rolf; POU, Sovitj; LI, Yuexin; KELLY, Jane Xu; FORQUER, Isaac; DOGGETT, J. Stone; BRUZUAL, Igor; FRUEH, Lisa; DODEAN, Rozalia; SMILKSTEIN, Martin; ALDAY, Holland; KOOP, Dennis; BLEYLE, Lisa; (43 pag.)WO2017/15360; (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 40546-94-9 as follows. Application In Synthesis of 6-Methyl-4-phenylchroman-2-one

Example 1[149] Preparation of 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid; [150](H) (HI)[152] [153] A reaction mixture of 0.75 kg 3,4-dihydro-6-methyl-4-phenyl-2H-benzopyran-2-one, 0.262 kg sodium hydroxide and 0.93 L DM water was stirred at 55-65C for 2-3 hrs. The reaction was cooled to RT. 0.825 kg dimethylsulphate was added drop wise to reaction mixture within 1-2 hr. After the completion of addition, reaction mixture was stirred at same temperature for 1-2 hrs. Again solution of 0.186 kg sodium hydroxide in 0.93 L DM water was added at RT within 1 hr. The reaction mixture was stirred at 70-800C for 3-5 hrs. After completion of reaction, reaction was cooled to RT. 0.3 L Cone, hydrochloric acid was added drop wise to the reaction mixture till washing is neutral. The reaction mixture was stirred for 1-2 hrs, then filtered &; washed with 2.0 L DM water to obtain wet cake. The wet cake was dried at 55-600C for 10-12 hrs to obtain 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid.[154] (Yield: 0.71 kg, 83%). [155] HPLC Purity: >; 95 %.

According to the analysis of related databases, 40546-94-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALEMBIC LIMITED; PONNAIAH, Ravi; DESAI, Sanjay; SHAH, Chankrakant Chunilal; PATEL, Kalpesh Shantibhai; PAREKH, Viral Maheshbhai; WO2010/92500; (2010); A2;,
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Application of 89-71-4, 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 89-71-4 as follows.

A mixture of methyl o-toluate (13.5 g, 89.9 mmol), NBS (17.6 g, 98.9 mmol), and benzoyl peroxide (50 mg, 0.2 mmol) in carbon tetrachloride (250 mL) was heated at reflux over the weekend. The reaction mixture was allowed to cool, and it was then filtered. The solvents were evaporated under reduced pressure and the residue was purified by chromatography, eluting with 3% ethyl acetate/hexanes to give 2-bromomethyl-benzoic acid methyl ester (7.7 g, 37%) as a white solid. 1HNMR (CDCl3): delta 7.97 (dd, J=1.5 Hz, 8.0 Hz, 1H), 7.49 (m, 2H), 7.38 (dt, J=1.5 Hz, 8.0 Hz, 1H), 4.96 (s, 2H), 3.94 (s, 3H). MS (APCI+): 231 (100), 229 (93).

According to the analysis of related databases, 89-71-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chu, Chang An; Gillespie, Paul; Tilley, Jefferson Wright; US2004/266856; (2004); A1;,
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79669-50-4, name is methyl 5-bromo-2-methyl-benzoate, 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. Computed Properties of C9H9BrO2

(2) A suspension of 1.19 g (9.46 mmol) of phenylboronic acid, 1.97 g (8.60 mmol) of methyl 5-bromo-2-methylbenzoate, 4 mg (0.017 mmol) of palladium (II) acetate, 2.97 g (21.5 mmol) of potassium carbonate, and 2.77 g (8.6 mmol) of tetrabutylammonium bromide in 20 ml of water was vigorously stirred under a stream of nitrogen, and stirred at 70 C. under an atmosphere of nitrogen for 1 hour. Water was added to the reaction mixture and it was extracted with tert-butyl methyl ether. The organic layer was dried and concentrated. The residue (1.9 g) was subjected to silica gel column chromatography (eluted with n-hexane:ethyl acetate=30:1) to obtain 1.65 g (7.29 mmol) of methyl 5-phenyl-2-methylbenzoate as an oil.

The synthetic route of 79669-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; US6489487; (2002); B1;,
Ester – Wikipedia,
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