Tag: M.W=200-300

653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, 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. 653-92-9

Example 9A methyl 4-fluoro-2-phenoxybenzoate Methyl 2-bromo-4-fluorobenzoate (1 g), phenol (0.565 g), cesium carbonate (1.96 g), copper(I) triflate toluene complex (0.087 g), and ethyl acetate (0.034 mL) in toluene (12 mL) was stirred at 110 C. for 24 hours. The reaction was cooled and chromatographed on silica gel with 5% ethyl acetate/hexanes.

Statistics shows that 653-92-9 is playing an increasingly important role. we look forward to future research findings about Methyl 2-bromo-4-fluorobenzoate.

Reference:
Patent; ABBOTT LABORATORIES; US2010/184750; (2010); A1;,
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24398-88-7, These common heterocyclic compound, 24398-88-7, name is Ethyl 3-bromobenzoate, 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: A mixture of copper powder (63.5 mg, 1.00 mmol), the aryl halide (500 mumol), 2-aminoethanol (74.9 muL, 1.25 mmol), and TMSN3 (133 muL, 1.00 mmol) in DMA (1 mL) in a 15 mL test tube was stirred under an Ar atmosphere (balloon) at 95 C using a Chemistation personal organic synthesizer (EYELA, Tokyo). After complete consumption of the aryl halide was confirmed by TLC analyses or after 24 h (if the reaction was incomplete within 24 h), the mixture was diluted with EtOAc (10 mL) and then filtered through a Celite pad. The pad was successively washed with EtOAc (20 mL), H2O (25 mL), and concd aq ammonia solution (5 mL). After the two layers were separated, the aqueous layer was extracted with EtOAc (2¡Á10 mL). The combined organic layers were washed with brine (20 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography with n-hexane/EtOAc or n-pentane/Et2O as the eluent.

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 24398-88-7.

Reference:
Article; Maejima, Toshihide; Shimoda, Yutaka; Nozaki, Kei; Mori, Shigeki; Sawama, Yoshinari; Monguchi, Yasunari; Sajiki, Hironao; Tetrahedron; vol. 68; 6; (2012); p. 1712 – 1722;,
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3469-00-9, name is Methyl Diphenylacetate, 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. 3469-00-9

General procedure: 4.2 General procedures: A. Microwave. Neat samples of amine (1.00 mmol) and carboxylic derivative (methyl ester or acid, 1.00 mmol) and DABAL-Me3 (202 mg, 0.8 equiv) were placed in a 5 mL microwave vial and dry THF added (1 mL) under a blanket of argon. For coupling partners containing acidic hydrogens additional DABAL-Me3 (total of 410 mg, 1.6 equiv) was used. The vial was promptly capped and placed in a CEM Discover microwave reactor. After irradiation (290 W, 130 C, 8 min) and programmed cool down (ca. 20 min). The reactions were quenched by cautious addition of HCl (2 M, 4 mL) or aqueous solutions of Rochelle salt (saturated potassium sodium tartrate, 4 mL) (CARE: methane liberated). Extraction with dichloromethane, drying (MgSO4) and evaporation frequently provided the pure products directly. If purification was required column chromatography 3:2 to 2:3 hexane:EtOAc was used for amides lacking highly polar functional groups (CH2Cl2 with 2 % v/v MeOH was used for amides bearing pendant amines, alcohols and other polar functional groups).

Statistics shows that 3469-00-9 is playing an increasingly important role. we look forward to future research findings about Methyl Diphenylacetate.

Reference:
Article; Dubois, Nathalie; Glynn, Daniel; McInally, Thomas; Rhodes, Barrie; Woodward, Simon; Irvine, Derek J.; Dodds, Chris; Tetrahedron; vol. 69; 46; (2013); p. 9890 – 9897;,
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A common heterocyclic compound, 619-42-1, name is Methyl 4-bromobenzoate, molecular formula is C8H7BrO2, 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. 619-42-1.

2.52a. methyl 4′-bromo-biphenyl-4-carboxylate 0.54 g (2.5 mmol) of methyl 4-bromo-benzoate is dissolved in 10 mL dioxane and 2.5 mL 2M-sodium carbonate solution. 0.6 g (3 mmol) of 4-bromophenyl-boric acid and 0.12 g (0.1 mmol) of tetrakis-(triphenylphosphine)-palladium are added successively and the reaction is refluxed for 5 hours. The reaction mixture is combined with water and EtOAc, filtered and the phases are separated. The aqueous phase is extracted with EtOAc and the combined organic phases are dried over MgSO4. After elimination of the drying agent and solvent the residue is triturated with acetonitrile, suction filtered and dried in the air. Yield: 100 mg (13.7% of theory); C14H11BrO2 (M=291.15); calc.: molar peak (M+H)+: 291/293 fnd.: molar peak (M+H)+: 291/293; Rf value: 0.68 (silica gel, petroleum ether/EtOAc 8:2).

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

Reference:
Patent; Boehringer Ingelheim International GmbH; US2004/242572; (2004); A1;,
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59247-47-1, Adding some certain compound to certain chemical reactions, such as: 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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 59247-47-1.

To a mixture of tert-butyl 4-bromobenzoate (10.07 g, 39.2 mmol), K3PO4 (20.19 g, 95 mmol), and dimethyl malonate (4.50 mL, 39.2 mmol) was added toluene (69 mL), Pd2(dba)3 (975 mg, 1.08 mmol), and .yen.(tert-Bu)3 (12.8 mL, 10percent wt. in hexanes, 4.3 mmol). The reaction mixture was degassed and heated to 85¡ãC. After 2 d, the reaction mixture was diluted with ethyl acetate, washed with water (1 x), brine (1 x), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5percent to 20percent ethyl acetate in hexanes) gave dimethyl [4-(fe/t-butoxycarbonyl)phenyl]malonate as a low melting white solid: 1HNMR (600 MHz, CDCl3) delta 7.98 (d, J = 8.5 Hz, 2H), 7.45 (d, J = 8.2 Hz, 2H), 4.70 (s, IH), 3.76 (s, 6H), 1.58 (s, 9H); ESIMS calcd 331.1 (Mi + Na), found 331.1 (Mi + Na).

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 59247-47-1.

Reference:
Patent; MERCK & CO., INC.; WO2007/55941; (2007); A2;,
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Ester – an overview | ScienceDirect Topics

609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, 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. 609-12-1

Into a 100-mL round-bottom flask, was placed 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.9 g, 10.0 mmol, 1.00 equiv), N,N-dimethylformamide (30 mL), ethyl 2-bromo-3-methylbutanoate (2.1 g, 10.0 mmol, 1.0 equiv), and cesium carbonate (10.0 g, 30.7 mmol, 3.0 equiv). The resulting solution was stirred for 12 hours at 90 C. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with ethyl acetate (20 mL*3), and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1:6). This resulted in 3.3 g (93%) of ethyl 3-methyl-2-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butanoate as a white solid.

Statistics shows that 609-12-1 is playing an increasingly important role. we look forward to future research findings about Ethyl 2-bromo-3-methylbutanoate.

Reference:
Patent; Arvinas Operations, Inc.; Genentech, Inc.; Crew, Andrew P.; Wang, Jing; Berlin, Michael; Dragovich, Peter; Chen, Huifen; Staben, Leanna; US2019/300521; (2019); A1;,
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Adding some certain compound to certain chemical reactions, such as: 1190-39-2, name is malonic acid dibutyl ester, 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 1190-39-2. 1190-39-2

General procedure: PhIO (550 mg, 2.5 mmol), Et3N¡¤5HF (800 mg, 4 mmol), and DCE (1 mL)were placed in a Teflon test tube. After stirring at r.t. for 15 min, the appropriate malonic ester 1 (1 mmol) and DCE (1 mL) were added. The test tube was sealed with a septum rubber and heated at 70 C for 24 h with stirring. The reaction mixture was neutralized with aq NaHCO3 and the product was extracted with CH2Cl2 (3 ¡Á 10 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure. The product was purified by column chromatography on silica gel with hexane-CH2Cl2 as eluent.

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 malonic acid dibutyl ester.

Reference:
Article; Kitamura, Tsugio; Muta, Kensuke; Oyamada, Juzo; Synthesis; vol. 47; 20; (2015); p. 3241 – 3245;,
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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, 653-92-9

General procedure: A sealed tube of 25 mL equipped with a magnetic stir bar was charged with alkynes (0.20 mmol), 2-bromobenzoic esters (0.22 mmol), CuI (0.02 mmol, 10 mol%), NaOH (0.4 mmol, 2 equiv) and CH3CN (1.0 mL). The reaction mixture was stirred at 100 C for 24 h. The reaction was monitored by GC or GC-MS. After completion of the reaction, the reaction mixture was cooled to room temperature, then washed with saturated NH4Cl aqueous solution (5.0 mL), and extracted with CHCl3 (3 * 5.0 mL). The combined organic phases were dried over Na2SO4 (anhydrous), concentrated in vacuum. The crude product was purified by flash column chromatography (eluent: ethyl acetate/petroleum ether = 1/20-1/10) on silica gel to afford the desired product.

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-bromo-4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sun, Mengli; Su, Lebin; Dong, Jianyu; Liu, Long; Zhou, Yongbo; Yin, Shuang-Feng; Tetrahedron Letters; vol. 58; 25; (2017); p. 2433 – 2437;,
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Adding a certain compound to certain chemical reactions, such as: 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, 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 23877-12-5, 23877-12-5

4-Hydroxybenzaldehyde (1) (5 g, 40.9 mmol) commercially available from Sigma-Aldrich was dissolved in N, N-dimethylformamide (50 mL) and potassium carbonate ), Magnesium sulfate (1.0 eq) and Tert-Butyl-a-bromoisobutyrate (5.0 eq) (R = -CH 3) were added in this order, and the mixture was stirred at 100 C for 22 hours. The reaction mixture was diluted with water and then extracted with ethyl acetate. The organic solvent layer was dried by adding anhydrous sodium sulfate, filtered, distilled, and purified by flash column chromatography to obtain the compound 2a (R = -CH3).

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, tert-Butyl 2-bromo-2-methylpropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Seoul National University R&DB Foundation; PARK, SEUNG-BUM; KOH, MIN-SEOB; KOO, JA-YOUNG; (32 pag.)KR101727634; (2017); B1;,
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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. 1186-73-8, name is Trimethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., 1186-73-8

Step 6; methyl 10-(((tert-butyldimethylsilyl)oxy)methyl)-l-(2,4-dimethoxybenzyl)-4- hydroxy-9-methyl-2-oxo-l,2,5,6,7,9-hexahydropyrido[3′,2′:6,7]cyclohepta[l,2- f] indole-3-carboxylate Crude N-(2-((tert-butyldimethylsilyloxy)methyl)-l-methyl-6,7,8,9- tetrahydrocyclohepta[fJindol-5(lH)-ylidene)-l-(2,4-dimethoxyphenyl)methanamine (10.6 g, 20.91 mmol) and trimethyl methanetricarboxylate (6.80 g, 35.76 mmol) were mixed together in PI12O (40 mL). With stirring, the mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after the initial bubbling of MeOH was observed (occurs at -160 C internal reaction temperature). The reaction mixture was cooled to room temperature, then purified by column chromatography (hexanes followed by EtOAc/hexanes 0-80% gradient) to yield the product as a yellow foam (7.44 g, 56%, 2 steps). XH NMR (500 MHz, CHCl3-i/) delta ppm 0.08 (s, 3 H) 0.09 (s, 3 H) 0.90 (s, 9 H) 1.45 – 1.55 (m, 1 H) 1.85 – 1.95 (m, 1 H) 1.96 – 2.05 (m, 1 H) 2.32 – 2.44 (m, 1 H) 2.58 (dd, J=13.4, 6.1 Hz, 1 H) 2.96 (dd, J=13.4, 5.4 Hz, 1 H) 3.33 (s, 3 H) 3.76 (s, 3 H) 3.78 (s, 3 H) 4.00 (s, 3 H) 4.80 (s, 2 H) 5.13 – 5.37 (m, 2 H) 6.22 (d, J=2.2 Hz, 1 H) 6.28 (s, 1 H) 6.34 (dd, J=8.4, 2.2 Hz, 1 H) 6.81 (d, J=8.4 Hz, 1 H) 7.06 (s, 1 H) 7.32 (s, 1 H) 13.66 (br. s, 1 H). LC-MS 633.5 [M+H]+, RT 1.85 min.

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; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
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