Month: January 2021

Synthetic Route of 2555-28-4, 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. 2555-28-4, name is 7-Methoxy-4-methylcoumarin belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-Methyl-6,7-dimethoxycoumarin (0.05 g, 0.227 mmol) was dissolved in acetonitrile (5 ml) in a microwave vessel. N-Bromosuccinimide (0.06 g, 0.340 mmol) was added to the mixture and the vessel inserted into the microwave at 250 W for 5 min at 80 C. The reaction was monitored by thin layer chromatography (silica gel, 3:1 CH2Cl2/EtOAc). Upon completion, the reaction mixture was cooled and the resultant precipitate was collected by vacuum filtration. The crude product was then recrystallized from a mixture of CH2Cl2/MeOH to yield 3-bromo-4-methyl-6,7-dimethoxycoumarin (1a, 0.060 g, 89%)

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, 7-Methoxy-4-methylcoumarin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Marriott, Karla-Sue C.; Bartee, Rena; Morrison, Andrew Z.; Stewart, Leonard; Wesby, Julian; Tetrahedron Letters; vol. 53; 26; (2012); p. 3319 – 3321;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

110661-91-1, name is tert-Butyl 4-bromobutanoate, 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. Recommanded Product: tert-Butyl 4-bromobutanoate

Intermediate 6 (10.47 g, 11.73 mmol) was dissolved in acetonitrile (500 ml) and tert-butyl bromoacetate (10.0 g, 44.84 mmol) and DIPEA (9.08 mg, 70.38 mmol) were added. The reaction mixture was stirred at RT for 14 days and then filtered. Evaporation of the solvent gave crude product which was purified using a Combiflash companion (120 g cartridge) eluting with 0-10% MeOH in DCM. The solid product was triturated with Et2O to give a white solid. Yield: 8.79 g (72%) LC-MS (Method 2): Rt = 2.93 min, m/z = 1036 [M+H]+

The synthetic route of 110661-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; WO2009/60206; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 5445-17-0, 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. 5445-17-0 name is Methyl 2-bromopropanoate, 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.

Example 22; Preparation of the Compound E-13; Preparation of ethyl 2-methyl-2-(2-methyl-4-(1-(3-(4-methyl-5-oxo-1-(4-trifluoromethyl-phenyl)-4,5-dihydrogen-1H-1,2,4-triazolyl))-benzylthio)-phenoxy)-acetate(E-13); In a 250 ml three-necked flask, to a stirred mixture of lithium aluminum tetrahydride (LiAlH4, 1.0 g, 26.4 mmol) and tetrahydrofuran (THF 30 ml) was added dropwise a solution of 3-methyl-4-hydroxy-phenyl thiocyanic acid (1.38 g, 8.35 mmol) in 20 ml of tetrahydrofuran at 0 C. After 30 min of stirring at 0 C., the mixture was allowed to warm up to room temperature and then stirred for another 2 hours at room temperature. The reaction was quenched by adding ethanol (10 ml). The value of pH of the mixture was adjusted to pH 3-4 by adding 6 N hydrochloric acid in an ice water bath, and then the aqueous phase was extracted with ethyl acetate (3¡Á80 ml). The combined organic layer was dried over anhydrous magnesium sulfate, filtrated, concentrated under reduced pressure, and purified by column chromatography (silica-gel H: 300-400 mesh; petroleum ether/ethyl acetate=5:1 v/v) to yield 1.44 g of a disulfide (yellow jelly-like liquid, yield: 62%).Its structure was characterized by the following data from nuclear magnetic resonance spectroscopy and Mass spectroscopy:1H NMR (400 MHz, CDCl3) delta 2.2 (s, 3H), 5.35 (s, 1H), 6.69 (d, J=8.28 Hz, 1H), 7.18 (dd, J=8.23 Hz, 2.23 Hz, 1H), 7.24 (d, J=2.24 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 15.7, 115.5, 125.0, 128.3, 130.2, 134.0, 154.4; MS (ESI) m/z 278.33 (M+H)+.In 250 ml single-necked flask, to a stirred solution of above crude product (0.7 g, 2.59 mmol) in acetonitrile (60 ml) were added methyl 2-bromo-propionate (0.7 ml, 6.0 mmol) and potassium carbonate (K2CO3, 2 g, 14.5 mmol). The resulting mixture was stirred at room temperature overnight. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (100 ml), and filtrated. The combined solution was evaporated under reduced pressure to give a residue which was purified by chromatography (silica-gel H: 300-400 mesh; petroleum ether/ethyl acetate=5:1 v/v) to yield 1.0 g of a yellow jelly-like liquid (yield: 86%).Its structure was characterized by the following data from nuclear magnetic resonance spectroscopy:1H NMR (400 MHz, CDCl3) delta 1.63 (d, J=6.84 Hz, 1H); 2.34 (s, 3H), 3.75 (s, 3H), 4.73 (q, J=6.84 Hz, 1H), 6.57-6.61 (m, 1H), 7.19-7.27 (m, 2H).In a 250 ml single-necked flask, to a stirred solution of the above-described product (1.0 g, 2.22 mmol) in ethanol (15 ml) were added 15 ml of water and 5 ml of concentrated hydrochloric acid. Zinc powder (10 g, 153 mmol) was added slowly. After the addition, the reaction mixture was stirred at room temperature for 30 min and then extracted with dichloromethane (3¡Á50 ml). The organic phases were combined, dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure to yield a pale-yellow liquid.In a 150 ml single-necked flask, to a stirred solution of the above crude product in 30 ml of acetonitrile were added a solution of 341-bromo-benzyl)-4-methyl-1-(4-trifluoromethyl)phenyl-1H-1,2,4-triazole-5(4H)-one (III-1) (1.8 g, 4.36 mmol) in acetonitrile (30 ml) and potassium carbonate (K2CO3, 2.5 g, 18.1 mmol). The reaction mixture was stirred at room temperature for 6 hours. After the reaction was completed, the reaction mixture was diluted by adding 100 ml of ethyl acetate, filtrated, concentrated under reduced pressure, and subjected to column chromatography (silica-gel H: 300-400 mesh; petroleum ether/ethyl acetate=5:1 v/v) to yield 1.2 g E-13 (a pair of diastereoisomers) (a pale-yellow jelly-like liquid, yield: 50%).Its structure was characterized by the following data from nuclear magnetic resonance spectroscopy:1H NMR (400 MHz, CDCl3) delta 1.61 (d, J=6.84 Hz, 1H); 2.18 (s, 3H), 3.15 (s, 3H), 3.70 (d, J=12.61 Hz, 3H); 4.70 (q, J=6.82 Hz, 1H); 5.18 (s, 1H); 6.51 (d, J=8.46 Hz, 1H), 7.0-7.11 (m, 1H), 7.10-7.15 (m, 1H), 7.34-7.37 (m, 5H), 7.67 (d, J=8.74 Hz, 2H), 8.11 (d, J=8.74 Hz, 2H); 13C NMR (100 MHz, CDCl3) delta 16.1, 18.5, 28.1, 50.6, 52.2, 72.7, 112.1, 118.2, 123.0, 125.5, 126.2, 126.8, 127.1, 128.2, 128.5, 128.9, 133.8, 135.2, 137.7, 140.6, 146.5, 152.6, 156.9, 172.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromopropanoate, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang Hisun Pharmaceutical Co., Ltd.; US2011/319458; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 73792-08-2, name is Methyl 4-amino-2-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 73792-08-2, name: Methyl 4-amino-2-fluorobenzoate

Add 2-fluoro-4-aminobenzoic acid methyl ester 2 (3.70 g, 21.8 mmol), cyclobutanone (2.44 g, 34.8 mmol), potassium cyanide (2.12 g, 32.6 mmol) and 37 mL to a 250 mL two-necked flask. Acetic acid, the temperature was raised to 80 C for 12 h, TLC monitoring reaction, (petroleum ether: ethyl acetate = 20:3), after the reaction was completed, 20 mL of water was added to the reaction solution, ethyl acetate extraction (30 ¡Á 3 mL), decompression In addition to the solvent, Compound 3, 5.01 g, brown red solid, yield: 92.5%.

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; Changsha Zeda Pharmaceutical Technology Co., Ltd.; Chen Yongheng; Xu Guangyu; Zhou Wenqiang; (23 pag.)CN108976171; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 2905-65-9, 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. 2905-65-9, name is Methyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Substituted benzoic acid (1.0 mmol) was dissolved in thionylchloride and refluxed for 2 h, then the solvent was removed underreduced pressure to obtain the white solid. The white solid in methanol was added concentrated sulfuric acid (1 mL) and themixture was refluxed for 4 h, the solvent was removed to obtaincrude solid. The crude solid was extracted with ethyl acetate andwater. The solvents were evaporated to afford the pure product.Finally, the pure product was dissolved in ethanol, and the hydrazinehydrate was added. The mixture was refluxed for 9 h, and thesolvent was removed

The synthetic route of Methyl 3-chlorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lian, Zhi-Min; Sun, Juan; Zhu, Hai-Liang; Journal of Molecular Structure; vol. 1117; (2016); p. 8 – 16;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 10259-22-0 as follows. Recommanded Product: Ethyl 3-methoxybenzoate

General procedure: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 mol%, 0.02 mmol) and CH3CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na2S2O3 (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a)

According to the analysis of related databases, 10259-22-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pramanick, Pranab Kumar; Hou, Zhen-Lin; Yao, Bo; Tetrahedron; vol. 73; 50; (2017); p. 7105 – 7114;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference 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.

SI- 16 (202 mg, 0.69 mmol, 1.2 eq.), COMU (296 mg, 0.69 mmol, 1.2 eq.), and N- methylmorpholine (190 pL, 1.7 mmol, 3 eq.) were dissolved in 1.5 mL DMF and incubated for 1 min. Amino-PEG3-t-butyl ester (160 mg, 0.58 mmol, 1 eq.) was added in 2.5 mL DMF and the reaction was stirred for 2h. The reaction was diluted with ethyl acetate (15 mL) and acidified with 1N HC1 to pH 3. The organic layer was washed with water (3x 25 mL) and brine (25 mL), dried over anhydrous MgS04, and concentrated under reduced pressure. The resulting residue was purified by flash chromatography to provide the title compound as a colorless oil (215 mg, 57%). NMR (500 MHz, Chloroform-if) d 7.66 (d, j= 8.7 Hz, 2H), 7.33 (d, j= 8.7 Hz, 2H), 6.97 (dd, J= 8.8, 7.2 Hz, 4H), 6.82 (d, J= 5.4 Hz, 1H), 3.63 (t, J= 6.5 Hz, 2H), 3.62 – 3.57 (m, 10H), 3.54 (td, J= 4.8, 4.4, 1.1 Hz, 2H), 2.43 (t, J= 6.5 Hz, 2H), 1.39 (s, 9H). HRMS (ESI) [M+H]+ for CieHseBrNiOe 551.1751, found 551.1751.

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; THE SCRIPPS RESEARCH INSTITUTE; ZHANG, Xiaoyu; CROWLEY, Vincent; CRAVATT, Benjamin; (121 pag.)WO2020/77278; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 4341-76-8 as follows. Product Details of 4341-76-8

General procedure: In a two neck rbf was stirred a mixture of Pd(OAc)2 (275 mg,1.22 mmol) and TDMPP (540 mg, 1.22 mmol) in benzene (30 ml)for 15 min at rt under nitrogen. To this mixture was added ethyl-2-butynoate 7 (2.84 ml, 24.48 mmol) and the resulting mixturewas further stirred for 10 min at rt. Next, ethynylbenzene 4a(2.50 g, 24.48 mmol) was added to this solution and the mixturewas stirred for 5-10 min until reaction was completed. Theworkup of reaction was performed by evaporating the solvent invacuum followed by column chromatography (Hexane:EtOAc = 100:1) to give the desired compound 8a (2.62 g);

According to the analysis of related databases, 4341-76-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Singh, Sarbjit; Goo, Ja-Il; Noh, Hyojin; Lee, Sung Jae; Kim, Myoung Woo; Park, Hyejun; Jalani, Hitesh B.; Lee, Kyeong; Kim, Chunsook; Kim, Won-Ki; Ju, Chung; Choi, Yongseok; Bioorganic and Medicinal Chemistry; vol. 25; 4; (2017); p. 1394 – 1405;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2033-24-1, name is 2,2-Dimethyl-1,3-dioxane-4,6-dione, 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 2033-24-1, category: esters-buliding-blocks

2,4,5-trifluorophenylacetic acid (30 g), tetrahydrofuran (360 ml_), 1 ,1 -carbonyl diimidazole (25.5 g) at about 5O0C, and meldrums acid (22.7 g) are combined. The mixture is stirred for about five hours at the same temperature. The reaction mass is then cooled to about 3O0C. Isopropyl acetate (180 ml_) and water (180 ml_) are added and stirred for about 30 minutes. The reaction mass is cooled to about O0C and pH is adjusted to about 2.4 using 36% aqueous hydrochloric acid. The organic layer is separated, washed with 0.1 N aqueous hydrochloric acid and distilled off completely. To the residue obtained, n-heptane (140 ml_) and isopropyl acetate (70 ml_) are charged at about 3O0C and stirred at about O0C for about 90 minutes. The separated solid is filtered and washed with a mixture of n-heptane (20 ml_) and isopropyl acetate (10 ml_). The wet cake is dried at about 5O0C for about 4 hours to afford the title compound. (Yield: 60.1 %; purity by HPLC: 98.0%)

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; DR. REDDY’S LABORATORIES LIMITED; DR. REDDY’S LABORATORIES, INC.; WO2009/85990; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 23426-63-3, 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. 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, This compound has unique chemical properties. The synthetic route is as follows.

A 3 neck round bottom flask equipped with a mechanical stirrer, thermometer, condenser and nitrogen bubbler, was charged with malononitrile (251 g, 3.80 moles) and THF (2 liters). t-BuOK (1 M THF, 3.80 L, 3.80 moles) was then added. The mixture was stirred at 50C for 0.5 h. Methyl 2-bromoisobutyrate (688 g, 3.80 moles) was added and the reaction mixture was stirred overnight at 50C. The reaction was partitioned between aqueous 1 N HCI and EtOAc. The organic phase was washed with brine, dried over anhyd. magnesium sulfate, filtered, and concentrated to afford the title compound. H NMR (400 MHz, CD3CN): delta 4.35 (1 H, s) 3.73 (3H, s), 1.43 (6H, s).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; GARFUNKLE, Joie; ORNOSKI, Olga; PARKER, Dann, L., Jr.; RAGHAVAN, Subharekha; XU, Libo; (88 pag.)WO2016/191334; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics