Tag: M.W=200-300

Related Products of 148547-19-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 148547-19-7 name is Methyl 4-bromo-3-methylbenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Preparation 17; 3-(4-lodomethyl-2-methyl-phenyl)-propionic acid methyl ester; Step A; 3- (4-Hydroxvmethyl-2-methyl-phenyl)-acrylic acid methyl ester; A mixture of methyl-4-bromo-3-methylbenzoate (5.7 g, 24.88 mmol), lithium aluminum hydride (29 mL, 29 mmol, 1 M solution in tetrahydrofuran) and tetrahydrofuran (100 mL) is stirred in ice/water for 1 hr. The reaction is quenched with aqueous hydrochloric acid (50 mL, 1 M). The product is extracted into ethyl acetate (3 X 100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product is taken up in propionitrile (100 mL). Methylacrylate (10 mL, 121.5 mmol), palladium acetate (1.12 g, 5 mmol), tri-o- tolylphosphine (3.0 g, 10 mmol), and N, N-diisopropyl ethylamine (8.7 mL, 50 mmol) are sequentially added and the resulting reaction mixture is heated to 110 deg C 3 hr. The mixture is concentrated, and the residue diluted with aqueous hydrochloric acid (100 mL, 1M). The product is extracted with dichloromethane (2 X 100 mL) and ethyl acetate (100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica chromatography eluting with 7: 3 hexanes: ethyl acetate to 1: 1 hexanes: ethyl acetate to afford the pure product as a yellow oil, 4.7 g, 91 %. MS M++1 207. The structure is confirmed by 1H NMR spectroscopy.

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/66136; (2005); A1;,
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Reference of 88709-17-5, 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. 88709-17-5, name is Ethyl 2-ethoxy-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl 2-ethoxy-4-methylbenzoate 117 (10.0 g, 48.1 mmol) in a mixture of pyridine (25 mL) and water (75 mL) was added KMn04 (22.8g, 144.2 mmol). The resulting mixture was heated at 50 C for 48 hours, then cooled and allowed to stir at room (0540) temperature for 24 hours. The mixture was filtered and the filter cake washed with hot water. The combined aqueous filtrates were washed with EtOAc (75 mL x 3) and acidified with 2M aqueous HCI solution. The mixture was extracted with CH2CI2 (150 mL x 3). The combined organic layers were washed with brine, dried (Na2S04), filtered and concentrated to give the desired compound as a white solid (5.0 g, 44%): LCMS: RT 0.25 min; m/z 239.0 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-ethoxy-4-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul Anthony; (88 pag.)WO2017/153519; (2017); A1;,
Ester – Wikipedia,
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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. 14062-30-7, name is Ethyl 2-(3-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Ethyl 2-(3-bromophenyl)acetate

Method A (3-Cyano-phenyl)-acetic acid ethyl ester To a mixture of of (3-bromo-phenyl)-acetic acid ethyl ester (15.3 g, 62.9 mmol) and 1-methyl-2-pyrrolidinone (125 mL) was added copper (I) cyanide (8.46 g, 94.4 mmol). The reaction mixture was stirred in an oil bath at 190 C. for 1 h. The reaction was cooled to room temperature and was diluted with EtOAc and 2:1 H2O/NH4OH. The mixture was stirred for 10 minutes and was filtered through Celite. The aqueous layer was washed with EtOAc (2*). The organic solution was washed with 2:1 H2O/NH4OH until the aqueous extracts were no longer blue. The organic solution was dried over MgSO4, filtered and concentrated to afford (3-cyano-phenyl)-acetic acid ethyl ester (11.95 g). 1H NMR (400 MHz, CDCl3) delta7.51-7.58 (m, 3H), 7.43 (t, 1H), 4.16 (q, 2H), 3.63 (s, 2H), 1.25 (t, 3H).

According to the analysis of related databases, 14062-30-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US6344485; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 139102-34-4, name is Methyl 4-bromo-2-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H9BrO3

General procedure: To 2 dram, stir-bar equipped vials, were added the aryl bromides (1.0 equiv). A stock solution of Ir[dF(CF3)ppy]2(dtbbpy)PF6 (1.0 mol%) and carboxylic acid 5 (1.1 equiv) in DMF (0.15 M with respect to carboxylic acid 5) was prepared, and to this stock solution was added TMG (1.1 equiv). The resulting stock solution was kept under a blanket of nitrogen. A separate solution of [Ni(dtbbpy)(H2O)4]Cl2 (10 mol%) in DMF (0.04 M) was prepared. The stock solution of Ir cat./acid/TMG was added to the aryl bromide monomers, followed by the Ni stock solution. The reaction mixtures were purged by blowing nitrogen over the top, sealed, and irradiated with blue LED (34 W LED Kessil lamps) for 24 h at room temperature. The reaction mixtures were diluted with EtOAc (3 mL) and H2O (4 mL). The organic layer was separated and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography with a solvent gradient from 0%EtOAc/hexanes to 100% EtOAc/hexanes to deliver the title compound.

According to the analysis of related databases, 139102-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Suen, Linda M.; Wang, Cheng; Hunter, David N.; Mitchell, Helen J.; Converso, Antonella; Elmarrouni, Abdellatif; Synthesis; vol. 50; 16; (2018); p. 3177 – 3186;,
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Reference of 609-12-1,Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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.

52.4 g of activated zinc powder and 450 ml of anhydrous THF,Add a few drops under N2 protectionEthyl alpha-bromoisovalerate2 to trigger the reaction,66 reflux 45min stirring until the reaction liquid becomes dark green after adding 20.324g (0.165mol)Cyclohexyl acetonitrile,And slowly add 2 (88.71 g, 0.4243 mol) within 1 h,Continue to reflow 1H stop heating, cooled to room temperature,Add 80ml 50% K2CO3 solution was stirred vigorously for 10min, the reaction solution was allowed to stratification, the organic phase was separated, the residue was extracted with THF,The combined organic phases were hydrolyzed by adding 150 ml of 15% HCl, the organic layer was separated and concentrated under reduced pressure, the aqueous layer was extracted three times with ethyl acetate,The combined organic phases were washed three times with saturated sodium bicarbonate solution, saturated NaCl, dried over anhydrous Na2SO4,The solvent was removed under reduced pressure to give compound 3 as a crude reddish brown liquid, 38.4 g, which was used directly in the next reaction without purification.

The synthetic route of 609-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yunnan University; Chinese Academy Of Sciences Kunming Animal Institute; He Yanping; Zheng Yongtang; Zhang Yufang; Xiang Siying; Zhang Hongbin; Zhao Zhidong; Yang Liumeng; (9 pag.)CN106866548; (2017); A;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14273-90-6, name is Methyl 6-bromohexanoate, 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 14273-90-6, Recommanded Product: 14273-90-6

6- (4-CHLORO-PHENYLSULFANYL)-HEXANOIC acid methyl ester (28b). To a solution of 6-bromohexanoic acid methyl ester (2.1 g, 10 mmol), triethylamine (1.6 mL, 11 mmol) and TERT-BUTYLAMMONIUM iodide (200 mg, 0.54 mmol) in freshly distilled THF (30 mL) was added 4-chlorothiophenol (1.45 g, 10 mmol) under an atmosphere of argon. The mixture was stirred at reflux for 2 hours after which it was concentrated under reduced pressure. The oil was dissolved in ethyl acetate (100 mL) and then washed successively with saturated aqueous sodium hydrogen carbonate (50 mL), distilled water (50 ML) and brine (50 mL). The organic layer was then dried over anhydrous MGS04, filtered and concentrated under reduced pressure to give an yellow oil that was purified by flash chromatography (1: 9 diethyl ether: 40-60 °C petroleum ether). The title compound was obtained as a colourless oil (2.5 g, 93percent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 6-bromohexanoate, and friends who are interested can also refer to it.

Reference:
Patent; QUEEN MARY & WESTFIELD COLLEGE; UNIVERSITY COLLEGE LONDON; BARTS AND THE LONDON NHS TRUST; WO2004/46094; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 35120-18-4, 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 35120-18-4 as follows.

Na2S?9H2O (182mg, 0.75mmol) was added to a solution of compound 5-b (180mg, 0.5mmol) in DMF (2mL).The mixture was reacted in a microwave at 130h for 1h, cooled to room temperature, 1-bromo-cyclobutanoic acid ethylester (155mg, 0.75mmol) was added, the mixture was stirred at 50h for 2hrs. The mixture was cooled to room temperature,followed by adding ice water (20mL), being extracted with EA (50mL). The organic phases were combined, dried overanhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica preparativeplate (PE:EA = 1:1) to give white solid 24-a (89 mg, yield 40%). LC-MS (ESI): m/z = 439 [M+H]+.

According to the analysis of related databases, 35120-18-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Yingli Pharmaceutical Co. Ltd.; XU, Zusheng; ZHANG, Nong; SUN, Qingrui; WU, Tianzhi; (104 pag.)EP3275867; (2018); A1;,
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Application of 773134-84-2, The chemical industry reduces the impact on the environment during synthesis 773134-84-2, name is Ethyl 1-bromo-2-naphthoate, I believe this compound will play a more active role in future production and life.

86.3g of (362.55 mmol) of 9,9-dimethyl-fluorene-2-boronic acid,92g (329.59 mmol) of ethyl bromonaphthalene-2-carboxylate 159.4g of (692 mmol)Tripotassium phosphate monohydrate,450ml of toluene,And dioxane of 230mlSuspended in water 700mlIt is,6.0g of (19.8 mmol)Tris -o- tolyl phosphineFollowing,Palladium acetate 740 mg (3.3 mmol) was added,Mixture,It is heated for 4 hours boiling.The organic phase is isolated,It is filtered through silica gel,It is vacuum evaporation.The residue,It is recrystallized from heptane.Yield: colorless solid 100.6g (78%).

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, Ethyl 1-bromo-2-naphthoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; BUESING, ARNE; STOESSEL, PHILIPP; HEIL, HOLGER; (94 pag.)JP5666130; (2015); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 26759-46-6, A common heterocyclic compound, 26759-46-6, name is Methyl 2-amino-4,5-dimethoxybenzoate, molecular formula is C10H13NO4, 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 1a,b (10 mmol) and methyl 2-amino-4,5-dimethoxybenzoate (12 mmol, 2.52 g), freshly prepared fused sodium acetate (0.3 g) was heated in a boiling water bath in glacial acetic acid (10 mL) for 3 h. The crystalline product separated on cooling was filtered, washed with water, dried, and recrystallized from ethanol.

The synthetic route of 26759-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Georgey, Hanan; Molecules; vol. 19; 3; (2014); p. 3777 – 3792;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 183322-16-9, 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. 183322-16-9, name is Ethyl 3,4-bis(2-methoxyethoxy)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of the compound (iii) (172.6g) was dissolved in acetic acid (954.1g) and stirred until clear dissolution. Under ice conditions Concentrated sulfuric acid (33.2g). Was added dropwise 65% nitric acid (160.8g). After completion of the dropwise addition, the reaction at room temperature for about 18H, seized by HPLCMeasuring the reaction was completed. Water was added l48g, (873gX3 times) and extracted with toluene, washed with sodium bicarbonate (2mol / L) and the pH adjusted left 8Right, once, the combined organic phase was washed once with sodium bicarbonate solution and extracted with 350g of toluene saturated brine (1048g). Spin-dry solventCompound (iv) (196 · 4g), yield 99%, purity> 95%

The chemical industry reduces the impact on the environment during synthesis Ethyl 3,4-bis(2-methoxyethoxy)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Zhejiang Apeloa Kangyu Pharmaceutical Co.,Ltd; Shanghai Yuyuan Bio-Pharma Co. Ltd; FENG, LICHUN; LI, QIEQIE; (11 pag.)CN103709110; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics