Month: February 2021

Electric Literature of 346603-63-2, The chemical industry reduces the impact on the environment during synthesis 346603-63-2, name is Methyl 2-methyl-3-(trifluoromethyl)benzoate, I believe this compound will play a more active role in future production and life.

To a solution of 2-methyl-3-trifluoromethyl-benzoic acid methyl ester (0.95 g, 4.35 mmol) in benzene (10 mL) was added N-bromosuccinimide (0.77 g, 4.33 g) and benzoyl peroxide (0.052 g, 0.21 mmol) and the resulting mixture heated to reflux for 4 h, cooled and stirred at room temperature for 48 h. The mixture was filtered, the filter cake washed with diethyl ether and the filtrate washed with a 1 N sodium thiosulfate solution (10 mL), brine and dried over magnesium sulfate. The mixture was filtered and evaporated and the residue purified via automated flash chromatography (Analogix, SF25-80 g column, 5->10% ethyl acetate/hexane gradient) to give 2-bromomethyl-3-trifluoromethyl-benzoic acid methyl ester (1.04 g, 3.50 mmol, 81%) as an off white solid; 1H NMR (300 MHz, DMSO-d6) delta ppm 3.72-4.16 (m, 3H), 5.03 (s, 2H), 7.47-8.32 (m, 3H).

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-methyl-3-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Berthel, Steven Joseph; Kester, Robert Francis; Orzechowski, Lucja; US2012/283271; (2012); A1;,
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1117-71-1, name is Methyl 4-bromobut-2-enoate, 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. Quality Control of Methyl 4-bromobut-2-enoate

To the suspension of potassium phthalimide (4.5 mmol) in dry DMF (4 mL) was added a solution of (E)-alkyl -bromobut-2-enoate in dry DMF (3 mL). The reaction was run at room temperature overnight. After the reaction was omplete, the reaction mixture was poured into water and extracted with ether and concentrated in vacuum to leave a hite solid. The residue can be easily purified by flash chromatography (petroleum/ethyl acetate, 4:1), to give the desired compounds 1.

The synthetic route of 1117-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Fuzhong; Chen, Jun; Zhang, Xiangyang; Liu, Jibing; Cun, Linfeng; Zhu, Jin; Deng, Jingen; Liao, Jian; Tetrahedron Letters; vol. 52; 7; (2011); p. 830 – 833;,
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Synthetic Route of 36692-49-6, 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. 36692-49-6, name is Methyl 3,4-diaminobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In 25 ml round-bottomed flask, a mixture of 1,2-phenylendiamine (1 mmol), a-bromoacetophenone(1 mmol) and BAILnano-SiO2 catalyst (35 mol%) was preparedand the reaction mixture was stirred at room temperature for the time shown inTable 2. The progress of the reaction was monitored by TLC. After completion of the reaction, ethyl acetate (5 mL) was added and the catalyst was separated by simplefiltration. The residue was dried over anhydrous Na2SO4 and after evaporation ofsolvent the pure product was obtained by recrystallization from ethanol.

The chemical industry reduces the impact on the environment during synthesis Methyl 3,4-diaminobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Daragahi, Seyed Arash Hosseini; Mohebat, Razieh; Mosslemin, Mohammad Hossein; Organic Preparations and Procedures International; vol. 50; 3; (2018); p. 301 – 313;,
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Reference of 41841-16-1,Some common heterocyclic compound, 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, molecular formula is C9H9BrO2, 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.

Methyl 2-(4-bromophenyl)acetate (1.00 g, 4.37 mmol)Dissolved in anhydrous DMF (12.5mL),The reaction solution is under N2 protection,Add NaH (700 mg, 17.5 mmol, 60%) at 0 C.Stir for about 15 minutes,CH3I (1.62 mL) was added slowly.After the dropwise addition was completed, the reaction solution was further stirred at 0 C for 15 minutes.Then transfer to room temperature for 12 h.After the reaction with saturated ammonium chloride (20mL) The reaction was quenched and extracted with EA (20mL), the organic layer was washed with saturated brine (30 mL), thenAfter concentration under reduced pressure,To give the title compound as a yellow oily substance (1.12g, 99.8%).

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-(4-bromophenyl)acetate, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Xinchang; Ren Qingyun; Yan Guanghua; S ¡¤geerdeman; Zhang Yingjun; (200 pag.)CN109678859; (2019); A;,
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Electric Literature of 33842-16-9, The chemical industry reduces the impact on the environment during synthesis 33842-16-9, name is Methyl benzo[d][1,3]dioxole-4-carboxylate, I believe this compound will play a more active role in future production and life.

A solution of methyl benzo[ ][1 ,3]dioxole-4-carboxylate (0.4 g, 2.22 mmol) in methanol (8.0 mL) was treated with 2.0 M aqueous KOH (2.2 mL) and the solution stirred at rt for 3 hours. The mixture was concentrated to ~3 mL volume, diluted with water (5 mL) and acidified to pH ~3 using 2.0 M HCI. The resulting precipitate was removed by filtration, washed with water then diethyl ether and dried in vacuo to give benzo[ ][1 ,3]dioxole-4-carboxylic acid as a beige solid (0.38 g, 97%).1H NMR (400 MHz, DMSO-d6): delta = 7.28 (dd, J= 8.0, 1.2 Hz, 1H),6.97 (dd, J=8.0, 1.2 Hz, 1H),6.89 (t, J=8.0Hz, 1 H), 6.12 (s, 2H);13C NMR(100 Hz, DMSO-de) 165.5, 148.9, 148.5, 122.9, 121.6, 113.8, 112.5, 102.1.

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 benzo[d][1,3]dioxole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF QUEENSLAND; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH NEAR DUBLIN; O’NEILL, Luke; COLL, Rebecca; COOPER, Matt; ROBERTSON, Avril; SCHRODER, Kate; (379 pag.)WO2016/131098; (2016); A1;,
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Electric Literature of 344-14-9,Some common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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.

Example 224 Synthesis of dimethyl 2-((2-((4-(tert-butoxycarbonyl)-1H-1,2,3-triazol-1-yl)methyl)-6-cyclopropylimidazo[1,2-a]pyridin-8-yl)methyl)-2-fluoromalonate. To a solution of compound dimethyl 2-fluoromalonate (0.54 g, 3.6 mmol) in anhydrous DMF (10 mL) was added NaH (140 mg, 3.6 mmol, 60% in mineral oil) and the reaction was stirred at 0 C. for 0.5 h under N2 atmosphere. Then the solution of tert-butyl 1-((8-(chloromethyl)-6-cyclopropylimidazo[1,2-a]pyridin-2-yl)methyl)-1H-1,2,3-triazole-4-carboxylate (1 g, 2.5 mmol) in DMF (2 mL) was added, The resulting mixture was stirred at 80 C. for 16 h. The reaction was quenched with saturated aqueous NH4Cl solution (20 mL), and extracted with ethyl acetate (100 mL*2). The combined organic phases were dried over Na2SO4, evaporated to give the crude, which was purified with silica gel chromatography (DCM/MeOH=100/1) to give the dimethyl 2-((2-((4-(tert-butoxycarbonyl)-1H-1,2,3-triazol-1-yl)methyl)-6-cyclopropylimidazo[1,2-a]pyridin-8-yl)methyl)-2-fluoromalonate (1.1 g, 85%) as a yellow solids. ESI-MS [M+H]+: 502.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 2-fluoromalonate, its application will become more common.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
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Electric Literature of 2967-66-0, 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. 2967-66-0, name is Methyl 4-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

Several other esters, whose structure and names are described in Table 3, were hydro genated under the conditions described above using preformed RuCl2(L-I). Isolated yield are given in Table 4.Table 3: Structure and names of substrates usedTable 4: Hydrogenation of esters using RuCl2(L-I) EPO Sub.: Substrate as described in Table 3.Conv.: Conversion (in %, analysed by GC after silylation) of ester to alcohol after 2h30min.Reaction conditions: Substrate (20 mmol), H2 gas (50 bars), RuCl2(L-I) 0.05 mol%,NaOMe 10 mol%, THF (14 mL) at 1000C during 2h 30min.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-(trifluoromethyl)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; FIRMENICH SA; WO2006/106484; (2006); A1;,
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Synthetic Route of 35613-44-6, 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. 35613-44-6, name is Methyl 2-(2-aminophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 7.2 g of 4-chloro-7-trifluoromethylquinoline, 5.4 g of methyl 2- aminophenylacetate and 250 mL of acetonitrile is heated under reflux for 18 hours. The solvent is evaporated under reduced pressure and the residue extracted 3 times with 200 mL portions of hot water. The aqueous extract is rendered basic with 10% ammonium hydroxide whereupon the desired compound precipitated; it was recrystallized from aqueous ethanol yielding colorless needles with a melting point of 140-1410C.

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

Reference:
Patent; MILESTONE PHARMACEUTICALS INC.; WO2008/48577; (2008); 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. 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, A new synthetic method of this compound is introduced below., COA of Formula: C9H9BrO2

Dissolve NaH (140mg, 3.50mmol, 60mass%) under nitrogen protectionN,N-dimethylformamide (10 mL) was added to it under ice bathMethyl 2-(4-bromophenyl)acetate (200 mg, 0.87 mmol),After stirring for 30 min, iodomethane (0.33 mL, 5.2 mmol) was added.The reaction was allowed to warm to room temperature and stirred for 12 h.The reaction was quenched with water (20 mL), EtOAc (EtOAc)Wash with saturated brine (50 mL), dryThe title compound was obtained as a colorless oil (150 mg, 67%).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Liu Xinchang; Huang Jianzhou; Zhang Yingjun; S ¡¤geerdeman; (267 pag.)CN109111451; (2019); A;,
Ester – Wikipedia,
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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 17100-63-9 as follows. Safety of Methyl 4-bromo-3-methoxybenzoate

A suspension of methyl 4-bromo-3-methoxybenzoate (2.5 g; 10.2 mmol; 1.00 eq.), 4-methyl-3- thiopheneboronic acid (Aldrich 542393; 1.59 g; 11.2 mmol; 1.1 eq.), potassium carbonate (7.05 g; 51 mmol; 5 eq.) and Pd(PPh3)4 (1.18 g; 1 mmol; 0.1 eq.) in toluene (12.5 ml_) and water (12.5 ml.) was refluxed for 5 hours. The reaction mixture was cooled down to room temperature and filtered through a pad of celite which was further washed with touene (200 ml_). The filtrate was concentrated in vacuo and the residue taken up in Ethyl acetate (400 ml_). The organic layer was washed with sat. aq. NaHCC>3 (100 ml_), water (100 ml_) and brine (100 ml_) then dried over magnesium sulfate and concentrated in vacuo. The residue (2.3 g; 8.77 mmol; 1 eq.) was taken up in EtOH (69 ml_), sodium hydroxide (5M; 5.26 ml 26.3 mmol; 3 eq.) was added and the reaction mixture was stirred at 6O0C for one hour. After concentration in vacuo, the residue was taken up in water (200 ml_) and the aqueous phase was washed with Ethyl acetate then acidified to pH 2 with cone. HCI. The solution was concentrated to ca. 100 ml_ and the precipitate filtered off and dried to afford the title compound (1.81 g, 71 %) as a brown solid. HPLC (Method A) : Rt 3.99 min (purity 97.4%). LC/MS : 246.9 (M-H)”.

According to the analysis of related databases, 17100-63-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43890; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics