Author: Jessica.F

Related Products of 2672-58-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 1 1,3,5-Tris(hydroxymethyl)benzene A solution of trimethyl 1,3,5-benzenetricarboxylate (8.83 g, 0.035 M; Aldrich) in THF (125 mL) is added dropwise over a period of 45 minutes to a stirred mixture of lithium aluminum hydride (3.98 g, 0.105 M) and dry THF (150 mL) under a nitrogen atmosphere. The initial phase of the addition results in vigorous reaction and consequently the addition is very slow at first. As the ester solution is added, an orange mass forms when the drops came in contact with the LiAlH4 mixture. A yellowish-green mixture results and is stirred at room temperature. The excess LiAlH4 is quenched carefully by the addition of ethyl acetate and the resulting mixture is acidified with aqueous 2N HCl solution until the pH is <3 and aluminum salts have dissolved. The layers are separated and the aqueous layer is extracted 3 times with additional ethyl acetate and then with methylene chloride. The organic extract layers are dried (sodium sulfate), filtered, and concentrated under reduced pressure to give a white solid (2.98 g, 51%). Recrystallization from acetonitrile-methylene chloride gives the title compound as white crystals (1.13 g) which appear to be hygroscopic when collected by suction filtration. The crystals are dried several days over P2 O5 in a vacuum desiccator after which they have amp of 76.5-78 C. 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, Trimethyl benzene-1,3,5-tricarboxylate, other downstream synthetic routes, hurry up and to see. Reference:
Patent; The Upjohn Company; US5500417; (1996); A;,
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Electric Literature of 2459-25-8, The chemical industry reduces the impact on the environment during synthesis 2459-25-8, name is Methyl 2-naphthoate, I believe this compound will play a more active role in future production and life.

4a (1.54 g, 9 mmol) was dissolved in 30 ml of ethanol, hydrazine hydrate was added, and the reaction was refluxed overnight. The next day, TLC monitored the reaction completely. At room temperature, a yellow solid precipitated continuously. Concentrate to a small volume, ice bath for 30 minutes, and filter to obtain a solid. Drying gave 1.21 g of a yellow solid. Yield: 72%.

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

Reference:
Patent; Zhejiang University; Chen Jianzhong; Yang Bo; He Qiaojun; Pan Youlu; Ying Meidan; (29 pag.)CN108329232; (2018); A;,
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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. 63746-12-3, name is Dimethyl 4-aminoisophthalate, A new synthetic method of this compound is introduced below., Quality Control of Dimethyl 4-aminoisophthalate

To a mixture of (4-adamantan-1-yl-phenoxy)-acetic acid (229 mg, 0.8 mmol) and 4-aminoisophthalic acid dimethyl ester (301 mg, 1.4 mmol) were dissolved in DMF (5 mL), and EDCHCl (140 mg, 0.75 mmol), HOAt (163 mg, 1.2 mmol) and DIPEA (0.21 ml, 1.2 mmol) was added. The mixture was stirred overnight, and then partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=50:1) to give 4-[2-(4-Adamantan-1-yl-phenoxy)acetyl-amino]-isophthalic acid dimethyl ester as a white solid (281 mg, 76.3% yield). 1H-NMR (CDCl3, 300 Hz) 12.00 (1H, s, NH), 9.40 (1H, d, J=1.8 Hz, aromatic), 8.12 (1H, d, J=7.8 Hz, aromatic), 7.78 (1H, dd, J=8.1 & 1.8 Hz, aromatic), 7.33 (2H, m, aromatic), 7.03 (2H, m, aromatic), 4.65 (2H, s, OCH2CO), 3.97 (3H, s, OCH3), 3.95 (3H, s, OCH3), 2.09 (3H, m, adamantyl), 1.89-1.90 (6H, m, adamantyl), 1.72-1.82 (6H, m, adamantyl).

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; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/306078; (2009); A1;,
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Reference of 25415-67-2, 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. 25415-67-2, name is Ethyl 4-methylpentanoate, This compound has unique chemical properties. The synthetic route is as follows.

Tetrahydrofuran (35 ml) was cooled down to -70C under inert gas atmosphere. At this temperature, 4.44 ml (11.1 mmol) of n-butyllithium solution (2.5 M in hexanes) and then 0.51 ml (9.71 mmol) acetonitrile were added dropwise. After 3 min at -70C, 1 .1 5 ml (6.93 mmol) ethyl 4- methylpentanoate were added dropwise at such a rate that the temperature of the solution did not exceed -66C. The mixture was stirred for 2 h at -45C before 22.2 ml of 1 N hydrochloric acid were added dropwise. The reaction mixture was concentrated under reduced pressure, and the residue was mixed with diethyl ether. After filtration through silica gel, the filtrate was evaporated under reduced pressure to yield 1.05 g of the crude title compound, which was used in the next step without further purification.GC-MS (method 5): Rt = 3.23 min; MS (EIpos): m/z = 138 (M-H)+ ‘H-NMR (DMSO-dg): delta = 4.03 (s, 2H), 2.51 (t, 2H), 1.50 (sext, 1H), 1.38 (q, 2H), 1.35 (d, 6H) ppm.

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

Reference:
Patent; Bayer Schering Pharma AG; MICHELS, Martin; FOLLMANN, Markus; VAKALOPOULOS, Alexandros; ZIMMERMANN, Katja; TEUSCH, Nicole; LOBELL, Mario; ENGEL, Karen; WO2011/42367; (2011); A1;,
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Reference of 87808-49-9,Some common heterocyclic compound, 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate, 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.

3-Bromo-4-methoxycarbonylbenzoic acid[0095] 2-bromo-4-methylbenzoic acid methyl ester (10.00 g, 42.8 mmol), tetrabutyl ammonium bromide (345 mg, 0.86 mmol), ruthenium chloride trihydrate (86 mg, 0.43 mmol), dichloroethane (14 mL) and sodium hypochlorite 10% (115 mL) were mixed. The pH at the aqueous phase was adjusted to 9.0 by addition of 20% v/v H2SO4. The biphasic mixture was stirred for 2.5 hours, and meanwhile, NaOH 20% v/v was added to keep the pH at 9. The phases were separated and the aqueous phase was washed with DCM (3 × 50 mL), acidified with 20% H2SO4 and extracted with EtOAc (3 × 50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo to afford 3-bromo-4-methoxycarbonylbenzoic acid as a whitish solid (2.33 g, 21% yield). 1H-NMR (400 MHz, CDCl3): 8.38 (d, J = 1.5, 1H), 8.07 (dd, J = 8.1, 1.6, 1H), 7.84 (d, J = 8.1, 1H), 3.98 (s, 3H).

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-bromo-4-methylbenzoate, its application will become more common.

Reference:
Patent; Prous Institute for Biomedical Research, S.A.; Prous, Josep R.; Serradell, Neus; Munoz, Rosa; Flores, Ramon; Garcia-Delgado, Noemi; EP2573088; (2013); A1;,
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Reference of 18014-00-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 18014-00-1, name is Dimethyl 2,5-dibromoterephthalate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Preparation of 2,5-dithien-2-ylterephthalic acid dimethyl ester Dimethyl 2,5-dibromoterephthalate (6.09 g, 17.30 mmol) is dissolved in anhydrous THF (100 cm3), followed by the addition of 2-thienylzinc bromide (0.50 M in THF, 90 cm3, 45.0 mmol) and Pd(PPh3)4 (0.50 g, 0.43 mmol). The mixture is heated at 67 C. for 2 hours. After cooling, the reaction mixture is poured into water. The precipitate is collected by filtration and washed with water, methanol and diethyl ether then dried in vacuo, to yield the product as a pale yellow solid (5.41 g, 87%). 1H NMR (300 MHz, CDCl3): delta(ppm) 7.82 (s, 2H, Ar-H), 7.40 (dd, J=4.8 and 1.4 Hz, 2H, Ar-H), 7.07-7.12 (m, 4H, Ar-H), 3.78 (s, 6H, CH3); 13C NMR (75 MHz, CDCl3): delta(ppm) 168.1 (C=O), 140.3 (q), 133.6 (q), 133.4 (q), 131.9 (CH), 127.5 (CH), 127.0 (CH), 126.7 (CH), 52.6 (CH3); MS (m/e): 358 (M+, 100%), 327, 299, 240, 195.

The synthetic route of Dimethyl 2,5-dibromoterephthalate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2011/226999; (2011); A1;,
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These common heterocyclic compound, 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, 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. Safety of Methyl 2-(2-bromophenyl)acetate

General procedure: In a three neck round bottom flask, CaCl2 (1.12 g, 10.2 mmol) was dissolved in ethanol (50 mL) under argon atmosphere. The resulting solution was cooled to 0 ?C, followed by the addition of NaBH4 (0.19 g, 5.1 mmol) at the same temperature. The resulting suspension was allowed to stir at 0 ?C for 30 min, after which a solution of S5a (1.0 g, 3.4 mmol) in 60 mL of Ethanol was added at the same temperature. The resulting reaction mixture was allowed to stir at 0 ?C for another 30 min, and then at rt for 15 h. After 15 h, 50 mL of a mixture of water and dichloromethane (1:1) was added to the reaction mixture which was then sonicated for 1 h. The resulting mixture was then subjected to vacuumfiltration over celite. The filtrate was collected and evaporated under reduced pressure. 50 mL of water was added to the resulting crude, which was then extracted with three portions of dichloromethane (30 mL each). The combined organic layer was dried over Na2SO4, and evaporated under reduced pressure to afford S6 2-(2-bromo-4,5-dimethoxyphenyl)ethanol (S6a): Brown Oil; (2.56 g, 60 %). 2-(2-bromo-5-methoxyphenyl)ethanol (S6b): Clear Oil; (1.29 g, 42 %). 2-(2-bromo-4-methoxyphenyl)ethanol (S6c): Clear Oil; (1.03 g, 55 %). 2-(2-bromophenyl)ethanol (S6d): Clear Oil; (2.41 g, 55 %).

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

Reference:
Article; Kapadia, Nirav; Harding, Wayne; Tetrahedron; vol. 69; 42; (2013); p. 8914 – 8920;,
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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 2967-93-3 as follows. Formula: C9H9FO2

Step 2; Preparation of 2-Fluoro-5-formyl-benzoic acid methyl ester; Add Af-bromosuccinimide (2.46 g, 13.86 mmol) and benzoyl peroxide (0.152 g, 0.630mmol) to a solution of 2-fluoro-5-methyl-benzoic acid methyl ester (1.06 g, 6.30 mmol)in carbon tetrachloride (50 mL). Heat the mixture at reflux for 4 h. Cool the mixture toroom temperature and wash with saturated aqueous sodium bicarbonate solution (10 mL)and brine (10 mL). Dry the organic layer over anhydrous sodium sulfate, filter, andconcentrate under reduced pressure. Dissolve the resulting residue in dimethylsulfoxide(30 mL) and heat at reflux for 16 h. Cool the mixture to room temperature and dilutewith water (100 mL) and ethyl acetate (100 mL). Extract the aqueous layer with ethylacetate (3 x 100 mL). Wash the combined organic layers with water (3 x 100 mL),followed by brine (100 mL). Dry the organic layer over anhydrous sodium sulfate, filterand concentrate. Purify the residue by chromatography over silica gel, eluting withhexanes/ethyl acetate (80:20), to provide the title compound as a tan solid (0.228 g, 20%).

According to the analysis of related databases, 2967-93-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/2342; (2006); A1;,
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Electric Literature of 210530-71-5, 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 210530-71-5 as follows.

To a stirred mixture of methyl 2- (3, 4-difluorophenyl) acetate (4.5 g, crude) in CCl4 (50 mL) was added NBS (6.0 g, 33.7 mmol) and HBr/HOAc (1.0 mL) . After the addition, the reaction mixture was stirred for 3 hours at 85. The solid of the reaction was filter out, the filtrate was concentrated, and this residue was dissolved by H2O (50 mL) , extracted with EtOAc (50 mL x 3) , The combined organic layers were washed with brine, dried over Na2SO4, concentrated to give methyl 2-bromo-2- (3, 4-difluorophenyl) acetate (4.0 g, crud) as a yellow oil. MS: M/e 266 (M+1)+

According to the analysis of related databases, 210530-71-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; SUN, Hanzi; ZHOU, Changyou; (253 pag.)WO2020/20097; (2020); A1;,
Ester – Wikipedia,
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Application of 167760-75-0,Some common heterocyclic compound, 167760-75-0, name is Methyl 4-amino-3-(trifluoromethyl)benzoate, molecular formula is C9H8F3NO2, 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.

Sodium nitrite (1.21 g, 0.017 mmol) was added to tetrafluoro boric acid (20 mL) in lot wise manner at -10C. The solution was stirred for 1 h at same tempreture then added methyl 4- amino-3-(trifluoromethyl)benzoate (3.5 g, 0.0 15 mmol) and continued stirring for h at sametempreture followed by addition of solution of KI (3.18 g, 0.0 19 mmol) in acetone : water (40 mL:60 mL).The reaction mass was stirred at rt for 1 h. The reaction mass was diluted with water and filtered to afford 4.8 g of title compound. ?H NMR (300 MHz, CDC13): 8.28 (s, 1H), 8.15-8.12 (d, J= 8.1Hz, 1H), 7.84-7.81 (d, J= 8.1Hz, 1H), 3.95(s, 3H).

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-amino-3-(trifluoromethyl)benzoate, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; KADAM, Sheetal R; (303 pag.)WO2016/55947; (2016); A1;,
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