Esters-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 144267-96-9, name is Ethyl 3,4-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 144267-96-9, Quality Control of Ethyl 3,4-difluorobenzoate

Intermediate 513-Fluoro-4-(2-methyl-1 H-imidazol-1 -yl)-benzoic acidTo a solution of ethyl 3,4-difluorobenzoate (1 .5 g) in N,N-dimethylformaide (12 mL) is added 2-methylimidazole (1 .3 g) and K2CO3 (2.2 g) and the mixture is heated at 140 C in a microwave oven for 1 h. After cooling to room temperature, water and ethyl acetate are added and the organic layer is dried (MgS04) and concentrated. The residue is purified by chromatography (ethyl acetate/hexane 0: 1?1 :0). The ester is dissolved in methanol (30 mL) and 4 M aqueous NaOH (3 mL) is added and the mixture is stirred at room temperature for 1 h. The mixture is neutralized with 6 M aqueous HCI, concentrated and then acidified with 6 M aqueous HCI. The precipitate is filtered off washing with a small amount of water and dried by suction to give the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3,4-difluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; HECKEL, Armin; BLUM, Andreas; BREITFELDER, Steffen; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; WELLENZOHN, Bernd; ASHWEEK, Neil, J.; HARRIOTT, Nicole; WO2012/123449; (2012); A1;,
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Related Products of 394-35-4, 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. 394-35-4, name is Methyl 2-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

0.06 mol of methyl o-fluorobenzoate,0.022 mol DIC,6.6 mmol DMAP was added to 100 mL dichloromethane, Stirring to continue stirring at room temperature for 30min,Gradually warming to 45 ~ 50 ,The reaction flask was charged with 1-cyclopropanecarbonylpiperazine (0.08 mol)Continue stirring reaction 9 ~ 10h.After the reaction is completed,Cool to 0 C and stir 45min,filter,The filtrate was washed with water (3 * 50 mL)Dried over anhydrous sodium sulfate,The methylene chloride was evaporated under reduced pressure,It was solid,Compound 2 (15.27 g),The yield was 92.57%Purity 99.92%

The chemical industry reduces the impact on the environment during synthesis Methyl 2-fluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shandong Yuxin Pharmaceutical Co., Ltd.; Liu Zhenteng; Sun Yiwei; Li Hua; Gong Wenju; Wang Libiao; (10 pag.)CN107325055; (2017); A;,
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Synthetic Route of 538372-37-1,Some common heterocyclic compound, 538372-37-1, name is Methyl 3,4-diamino-2-methoxybenzoate, molecular formula is C9H12N2O3, 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.

Compound 63E (1.3 g, 6.6 mmol)And 3,5-dichlorosalicylaldehyde (1.52 g, 7.95 mmol)Stirring in 25 mL of nitrobenzene for two hours, after cooling to room temperature,A large amount of precipitated precipitated, filtered, and the filter cake was washed with petroleum ether.Compound 63F (2.0 g, 85% yield) was obtained.

The synthetic route of 538372-37-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Chen Huanming; Liang Bo; Cao Wenjie; Zhang Guiping; Zhao Zhongqiang; Jiang Zhaojian; Zuo Gaolei; Xu Wanmei; Gong Hongju; Zhang Peng; Wang Jianghuai; Li Qingsong; Gao Chunhua; (79 pag.)CN104045552; (2019); B;,
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Electric Literature of 116419-94-4, These common heterocyclic compound, 116419-94-4, name is Methyl 4-methyl-3-(trifluoromethyl)benzoate, 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.

A solution of 4-methyl-3-trifluoromethylbenzoic acid (1.71 g, 8.37 mmol) in DMF (20 mL) was added with potassium carbonate (1.39 g, 10.1 mmol) and the reaction mixture was stirred at room temperature for five minutes. Iodomethane (0.78 mL, 12.5 mmol) was added and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine (¡Á2). The organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated at reduced pressure to afford methyl 4-methyl-3-trifluoromethylbenzoate. The material was dissolved in carbon tetrachloride (10 mL) and treated sequentially with N-bromosuccinimide (2.74 g, 15.4 mmol) and benzoyl peroxide (catalytic) and heated at 80 C. for 18 hours. The mixture was allowed to cool and diluted with water. The mixture was poured through a hydrophobic frit and the solvent evaporated at reduced pressure to afford methyl 4-(dibromomethyl)-3-trifluoromethylbenzoate. The material was dissolved in acetone/ water (25 mL/5 mL) and silver nitrate (2.38 g, 14.0 mmol) added. (0223) The reaction mixture was stirred at room temperature for 72 hours. The suspension was filtered through a pad of celite and the filtrate diluted with ethyl acetate. The solution was washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was dissolved acetone/water (25 mL/5 mL) and silver nitrate (2.38 g, 14.0 mmol) added. (0224) The reaction mixture was stirred at room temperature for 24 hours. The suspension was filtered through a pad of celite and the filtrate diluted with ethyl acetate. The solution was washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (eluent-100% i-hexane to 8:1 i-hexane/ ethyl acetate) to afford the title compound (0.537 g, 33%). (0225) 1H NMR (400 MHz, CDCl3); delta 10.46-10.45 (m, 1H), 8.46 (s, 1H), 8.35 (d, J=8.2 Hz, 1H), 8.20 (d, J=8.2 Hz, 1H), 4.00 (s, 3H).

Statistics shows that Methyl 4-methyl-3-(trifluoromethyl)benzoate is playing an increasingly important role. we look forward to future research findings about 116419-94-4.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; RANCATI, Fabio; Rizzi, Andrea; Carzaniga, Laura; Linney, Ian; Knight, Chris; Schmidt, Wolfgang; (120 pag.)US2018/16267; (2018); 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. 4934-99-0, name is Methyl 3-hydroxycyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 4934-99-0

To a solution of methyl 3-hydroxycyclobutanecarboxylate (1.2 g, 9.0 mmol) in DMF (20 mL) was added sodium hydride (60%> wt in mineral oil) (1.8 g, 45 mmol) at RT. The mixture was stirred for 1 h and then 2, 5-difluoro-3-(tetrahydro-pyran-4-yl)-pyridine (1.8 g, 9.0 mmol) was added. The reaction mixture was heated to 60 C for 3 h and then quenched with saturated NH4C1. The solution was diluted with EtOAc and water and extracted with EtOAc (2xl0mL). The organic extracts were combined, washed with brine (lOmL), dried over MgS04, filtered, and concentrated to get a residue, which was purified by flash column chromatography on silica gel (5% to 30%> EtOAc in hexanes) to give the product (3.2 g) as yellow oil.

According to the analysis of related databases, 4934-99-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; FROHN, Michael; HARRINGTON, Paul; PICKRELL, Alexander; RZASA, Robert; SHAM, Kelvin; HU, Essa; WO2011/143366; (2011); A1;,
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Related Products of 685-88-1, These common heterocyclic compound, 685-88-1, name is Diethyl fluoromalonate, 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.

To diethyl 2 fluoromalonate ester (1.0 g, 5.617 mmol) was added ethanol (10 ml), water (10ml), and lithium hydroxide monohydrate (0.943 g, 22.47mmol), then the reaction was stirred well for 16h at 50C. Then the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted in MTBE and water, then mixture was acidify with 6N HCl and then extracted with MTBE (5 x 50 ml). The combined organic layer were dried over Na2SO4, filtered and concentrated under reduced pressure to give 400 mg (yield 58%) of a white solid corresponding to 2-fluoromalonic acid. The crude product used in the next step without further purification. Synthesis of 2,4-dichloro-3-fluoroquinoline, intermediate 348-I-2

The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENOSCIENCE PHARMA; BRUN, Sonia; BERET, Antoine; BASSISSI, Firas; HALFON, Philippe; COURCAMBECK, Jerome; (275 pag.)WO2017/191599; (2017); 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. 792-74-5, name is Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 792-74-5

General procedure: To a solution of benzo[b]thiophene (8) (2.15g, 16.0mmol) in 20ml dry THF under an argon atmosphere at?30¡ãC, n-BuLi (10.0ml, 16.0mmol, 1.6M n-hexane) was added slowly. The mixture was treated with the corresponding ester and stirred at room temperature. After quenching with saturated aqueous NH4Cl-solution, the residue was extracted with CHCl3. The organic phase was dried (Na2SO4) and the solvent evaporated.

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; Katzsch, Felix; Gruber, Tobias; Weber, Edwin; Journal of Molecular Structure; vol. 1114; (2016); p. 48 – 64;,
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Electric Literature of 252881-74-6, 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 252881-74-6 as follows.

Synthesis of tert-Butyl 1 -((3 S,4aS,6aR,6b S,8aS, 11S,1 2aR, 1 4aR, 1 4b S)- 11 -((benzyloxy)carbonyl)-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,1 4a, 1 4b-icosahydropicen-3 -yl)- 1 -oxo-5, 8,11 -trioxa-2-azatetradecan- 1 4-oate (110-1). Into a250-mL round-bottom flask, was placed 1-7 (515 mg, 0.85 mmol, 1.00 equiv), DCM (50 mL), tert-butyl 3-2-[2-(2-aminoethoxy)ethoxy]ethoxypropanoate (589 mg, 2.12 mmol, 2.50 equiv), TEA (0.885 mL, 7.50 equiv). The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with EtOAc/petroleum ether (1:1). This resulted in 533 mg (74%) of 110-1 as a lightyellow solid.

According to the analysis of related databases, 252881-74-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARDELYX, INC.; LUEHR, Gary; DRAGOLI, Dean; LEADBETTER, Michael; CHEN, Tao; LEWIS, Jason; (181 pag.)WO2019/60051; (2019); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 431-47-0, name is Methyl 2,2,2-trifluoroacetate, 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 431-47-0, Application In Synthesis of Methyl 2,2,2-trifluoroacetate

N-benzyl p-toluenesulfonamide (100 mg, 0.38 mmol), DMF (4 mL), potassium t-butoxide (129 mg, 1.15 mmol, 3 eq.) was added to the reaction flask in turn, and stirred at room temperature for 5 minutes. After the potassium tert-butoxide was uniformly dispersed, methyl trifluoroacetate (0.15 mL, 1.52 mmol, 4 eq.) was slowly injected into the reaction flask, and after 10 hours of reaction, stirring was stopped. It was extracted twice with ethyl acetate and distilled water, and then washed with a saturated NaCI solution. The magnesium sulfate was removed by filtration, and the solvent was evaporated. Purification by column chromatography to give N-methyl-N-benzyl-p-toluenesulfonamide (104 mg, yield 100%)

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; Guangdong Petrochemical College; Xiao Duoduo; Zheng Xin; Zeng Jiechun; Huang Jiawei; Zhou Rujin; Guan Ying; Liang Jieling; (8 pag.)CN109369506; (2019); A;,
Ester – Wikipedia,
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Reference of 33155-58-7, A common heterocyclic compound, 33155-58-7, name is tert-Butyl 2-(4-Bromophenyl)acetate, molecular formula is C12H15BrO2, 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.

To an N?-purged flask containing the title compound from the previous step (1.55 g, 5.55 mmol), were added PdCl2(PPh3)2 (584 mg, 0.83 mmol), w-BuOH (30 mL), and DIEA (5.00 mL, 27.8 mmol). The mixture was placed under an atmosphere of carbon monoxide and stirred vigorously at 110 0C. After 1 h, the reaction mixture was allowed to cool to room temperature, and was concentrated in vacuo. Purification by silica gel chromatography (0 to 100% EtOAc in hexanes) provided the title compound: LCMS (ESI): m/z 237.3 [M – tBu]+; 1H NMR (500 MHz, CDCl3): delta 7.99 (d, J = 8.0 Hz, 2 H)5 7.34 (d, J = 8.0 Hz, 2 H), 4.32 (t, J = 6.5 Hz, 2 H), 1.77-1.72 (m, 2 H), 1.51-1.45 (m, 2 H), 1.43 (s, 9 H), 0.98 (t, J = 8.0 Hz, 3 H).

The synthetic route of 33155-58-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2007/136577; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics