Tag: M.W=200-300

Some common heterocyclic compound, 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate, molecular formula is C7H11BrO2, 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. COA of Formula: C7H11BrO2

To the Schlenk sealed reactor was added p-methoxystyrene (0.2 mmol) of formula I-1, formula II-1N,N-dimethylaniline (2 equivalents), compound of formula III-4 (2 equivalents), CuCl (10 mol%), [Ru(bipy)3]Cl2·6H2O (2 mol%), K2CO3 (2 equivalents) and MeCN (1 mL), then protected with argon at room temperature and 3W blueLED light source reacts under light conditions. After monitoring the reaction by TLC or GC-MS, the solvent is distilled off under reduced pressure, and then the residue is removed.The residue was subjected to column chromatography (yield: n-hexane / ethyl acetate) to afford the desired product of formula IV-4. Yield 42%; colorless oilLiquid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35120-18-4, its application will become more common.

Reference:
Patent; Nanchang Hangkong University; Song Renjie; Yong Xin; Li Jinheng; (21 pag.)CN108675935; (2018); A;,
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Reference of 15964-79-1, A common heterocyclic compound, 15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)acetate, molecular formula is C11H14O4, 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.

l-(4-Bromovhenyl)-4-(3,4-dimethoxyphenyl)butane-l,3-dione; Sodium hydride (60% dispersion, 3.80 g, 95.1 mmol) was added portionwise to methyl 2-(3,4-dimethoxyphenyl) acetate (10 g, 47.6 mmol) in Et2O (100 ml) at O0C. A solution of 4′-bromoacetophenone (9.48 g, 47.6 mmol) in Et2O (50 ml) was added dropwise over 1 h. The mixture was heated at reflux for 16 h, cooled, poured into ice/HCl (2 M)5 extracted with Et2O (3 x 100 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was crystallized from MeOH to give the title compound (9 g, 50 %) as a tan powder.

The synthetic route of 15964-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ESSILOR INTERNATIONAL (COMPAGNIE GENERALE D’OPTIQUE); WO2008/29194; (2008); A1;,
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Reference of 957207-58-8, 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 957207-58-8 as follows.

To a 100 mL round-bottomed flask was added methyl 4-bromo-2-(trifluoromethyl)benzoate (2.25 g, 8.00 mmol), fluorovinyl) (methyl)diphenylsilane (3.58 g, 14.8 mmol), and 1,3-dimethylimidazolidin-2-one (40 mL). Tetrakis(triphenylphosphine)palladium(0) (0.459 g, 0.400 mmol), copper(I) iodide (0.0760 mg, 0.400 mmol), and cesium fluoride (3.62 g, 23.9 mmol) were added and the reaction was stirred at room temperature for 24 hours under a nitrogen atmosphere. Water was added to the mixture and the mixture was diluted with 3:1 hexanes/diethyl ether. The layer was separated, and the organic layer was dried over sodium sulfate, concentrated, and the residue was purified by flash column chromatography provided the title compound as a colorless oil (2.00 g, 96percent): 1H NMR (400 MHz, CDCl3) delta 7.96-7.87 (m, 1H), 7.83 (dq, J=8.1, 0.7 Hz, 1H), 7.77 (dd, J=8.2, 1.7 Hz, 1H), 5.23 (dd, J=48.6, 4.0 Hz, 1H), 5.07 (dd, J=17.4, 4.0 Hz, 1H), 3.95 (s, 3H); 19F NMR (376 MHz, CDCl3) delta?59.92, ?108.73 (d, J=1.4 Hz); EIMS m/z 248 ([M]+)

According to the analysis of related databases, 957207-58-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; Barton, Thomas; Gao, Xin; Hunter, Jim; LePlae, JR., Paul R.; Lo, William C.; Boruwa, Joshodeep; Tangirala, Raghuram; Watson, Gerald B.; Herbert, John; (90 pag.)US2017/208804; (2017); A1;,
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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 150726-89-9 as follows. Application In Synthesis of Dimethyl 2-(2-methoxyphenoxy)malonate

a) A solution of 10 g of dimethyl-(o-methoxyphenoxy)malonate (Example 1 b) in 80 ml dry methanol was cooled to 0 C. 6.71 g of sodium methylate was added portionenwise. To the suspension was added 2.84 g of acetamidine hydrochloride and the mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure and the residue was suspended in 100 ml of diethyl ether. The solid was filtered off, washed with another portion of 100 ml of diethyl ether and dissolved in 50 ml of water. The pH was adjusted to 4 by adding 25 ml of glacial acetic acid. The white precipitate that formed was filtered off, washed with water and dried to yield 5.17 g of 5-(o-methoxyphenoxy)-4,6-dihydroxy-2-methyl-pyrimidine (or a tautomer) as a white powder.

According to the analysis of related databases, 150726-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bolli, Martin; Boss, Christoph; Clozel, Martine; Fischli, Walter; US2003/87920; (2003); 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. 26050-64-6, name is Methyl 4-bromo-3,5-dimethoxybenzoate, A new synthetic method of this compound is introduced below., name: Methyl 4-bromo-3,5-dimethoxybenzoate

Intermediate 73b: methyl 3,5-dimethoxy-4-(prop-1-en-2-yl)benzoate To a solution of Intermediate 73a (6.0g, 21.9 mmol) in DMF (100 ml_) were added isopropenyltributylstanane (7.98g, 24.1 mmol), cesium fluoride (6.66g, 43.8 mmol), and Pd[(te/f-butyl)3P]4 (225 mg, 0.44 mmol). The reaction was heated in a 100 deg C bath for 3h, then cooled to ambient temperature. The reaction was diluted with water and extracted with ethyl acetate (2 x 100 ml_). The combined organic extractes were washed with brine, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified on silica gel with ethyl acetate and hexane as eluent to provide the desired compound. TLC (silica gel, 10% ethyl acetate in hexane): Rf = 0.45

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; NOVARTIS AG; BARYZA, Jeremy Lee; BECKWITH, Rohan Eric John; BOWMAN, Keith; BYERS, Crystal; FAZAL, Tanzina; GAMBER, Gabriel Grant; LEE, Cameron Chuck-Munn; TICHKULE, Ritesh Bhanudasji; VARGEESE, Chandra; WANG, Shuangxi; WEST, Laura; ZABAWA, Thomas; ZHAO, Junping; WO2014/136086; (2014); A1;,
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Related Products of 56441-97-5,Some common heterocyclic compound, 56441-97-5, name is Methyl 4-(benzyloxy)-3-methoxybenzoate, molecular formula is C16H16O4, 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.

34 ml of glacial acetic acid, fuming nitric acid (13.6 mmol, 5.8 ml) was added to a 100 ml round-bottomed flask and stirred at 0 C in an ice bath. Methyl 3-methoxy-4-benzyloxybenzoate 13.3 mmol, 3.7 g) was slowly added to the solution in portions and the reaction was continued at 0 C for 30 minutes and then at room temperature for 6 hours.The reaction solution was slowly poured into 120 ml of ice water, stirred to precipitate solid, filtered, washed with a small amount of ether and dried to give 4.0 g of yellow solid as 2-nitro-4-benzyloxy-5-methoxybenzene acid methyl ester, yield% 94.7

The synthetic route of 56441-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Sun, Liping; Zhang, Haiqi; Zhang, Chi; Gong, Feihu; Xu, Yungen; (18 pag.)CN105884699; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 148547-19-7, 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. 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 4-bromo-3-methylbenzoate (ABCR, 4.90 g; 21.39 mmol; 1 eq.), 2- methoxyphenylboronic acid (3.575 g; 23.53 mmol; 1.10 eq.), potassium carbonate (14.781 mg; 107 mmol; 5 eq.), tetrakis(tripnenylphosphine)palladium(0) (2.5 mg; 2.14 mmol; 0.10 eq.) were mixed in toluene (24.5 mL) and water (24.5 mL) under N2 atmosphere. The reaction mixture was degassed with N2for 10 min and was heated under reflux for 6 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with toluene (500 mL). The filtrate was concentrated under vacuum to afford brown oil. It was taken in EtOAc (500 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 (200 mL), water (200 mL) and brine (200 mL). It was dried over MgSO4, filtered off and concentrated under vacuum giving a brown oil. It was purified by flash chromatography (cHex/EtOAc 9:1 ), affording the title compound as a colorless oil (4.38 g, 80%). 1H NMR: (DMSO-d6, 300 MHz) delta 7.94 (s, 1 H), 7.89-7.86 (dd, J = 8.06 Hz, J = 1.61 Hz, 1 H), 7.51-7.46 (m, 1 H), 7.34-7.31 (d, J = 8.13 Hz, 1 H), 7.21 -7.09 (m, 3H), 3.95 (s, 3H), 3.79 (s, 3H), 2.19 (s, 3H). LC/MS (Method A): 257.0 (M+H)+. HPLC (Method A) Rt 4.85 min (Purity: 98.9%).

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 4-bromo-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 152849-72-4, 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. 152849-72-4, name is Methyl 5-bromo-2,4-dimethylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 3: Methyl 5-(1-(2-methoxyphenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate A mixture of methyl 5-bromo-2,4-dimethyl-benzoate (785.66 mg, 3.23 mmol), 1-(2-methoxyphenyl)piperidin-4-amine (800.00 mg, 3.88 mmol) in toluene (25.00 mL) was added BINAP (201.24 mg, 323.19 umol) and sodium tert-butoxide (621.16 mg, 6.46 mmol). The mixture was degassed for 3 mins, then, Pd2 (dba)3 (295.95 mg, 323.19 umol) was added. The resulting mixture was degassed for 3 mins. After that, the mixture was kept stirring at 90 C. for 18 h under N2. The mixture was diluted with EtOAc (60 mL), filtrated and concentrated in vacuo, the residue was purified by CombiFlash (UV254, silica gel, 40 g, EA/PE from 0% to 40% to give the desired product methyl 5-[[1-(2-methoxyphenyl)-4-piperidyl]amino]-2,4-dimethyl-benzoate (189.00 mg, 512.93 umol, 15.87% yield) as a yellow solid. ESI-MS (EI+, m/z): 369.3 [M+H]+. 1H NMR (500 MHz, MeOD-d4) delta 7.24 (s, 1H), 7.08-7.01 (m, 2H), 6.99-6.95 (m, 2H), 6.93 (td, J=7.6, 1.5 Hz, 1H), 3.89 (s, 3H), 3.87 (s, 3H), 3.52-3.40 (m, 3H), 2.78 (td, J=11.8, 2.1 Hz, 2H), 2.43 (s, 3H), 2.19 (s, 3H), 2.16 (d, J=12.6 Hz, 2H), 1.73 (td, J=14.3, 3.6 Hz, 2H).

The synthetic route of Methyl 5-bromo-2,4-dimethylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (519 pag.)US2018/127370; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, 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 154825-97-5, Application In Synthesis of Methyl 2-(4-bromophenyl)-2,2-dimethylacetate

methyl 3-bromophenyltert-butanoate (formula II) (257g), ethenyl benzyl ether (formula V) (140g), potassium carbonate (138g), and 1,4-dioxane (2L), Replaced 3 times with nitrogen, added tetratriphenylphosphine palladium (3g), and reacted at 100 C for 12h. The reaction was monitored by TLC for completion. The complete reaction system was reduced to room temperature, filtered, and concentrated to remove 1,4-dioxane. Water (1 L) ethyl acetate (1 L) was added, and the layers were separated. The organic phase was dried over anhydrous sodium sulfate and concentrated to dryness to give methyl 4-(2-benzyloxyethenyl)phenyltert-butanoate (formula III) (300 g), yield: 96.7%, purity: 98%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Tiancizhong Business Pharmaceutical Co., Ltd.; Chi Wangzhou; Li Hanpu; Ma Xilai; Li Yonggang; Sha Fei; (8 pag.)CN110734375; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 183322-16-9, name is Ethyl 3,4-bis(2-methoxyethoxy)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester (15.00 g, 0.05 mol) was added into acetic acid (50 ml) to form a mixture, and while the mixture was stirred in an ice water bath, 65%-68% nitric acid (13 ml) was added to the mixture. The mixture then was stirred for 24 h at room temperature. The reaction mixture was poured into ice water (500 ml), and extracted with ethyl acetate. The organic phase was combined, washed with saturated sodium bicarbonate solution three times, washed with saturated sodium chloride solution, and then dried by anhydrous sodium sulfate. The organic phase was then filtered to obtain a filtrate. The filtrate was concentrated to obtain a brown oily liquid 2-nitro-4,5-bis(2-methoxyethoxy)ethyl benzoate (14.10 g, 82.22%).

The synthetic route of 183322-16-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Salubris Pharmaceuticals Co., Ltd.; Shanghai Institute of Pharmaceutical Industry; LI, Jianqi; ZHANG, Zixue; XIE, Peng; ZHANG, Qingwei; EP2592083; (2013); A1;,
Ester – Wikipedia,
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