Tag: M.W=200-300

Synthetic Route of 6091-64-1, The chemical industry reduces the impact on the environment during synthesis 6091-64-1, name is Ethyl 2-bromobenzoate, I believe this compound will play a more active role in future production and life.

A mixture of bromide 2-bromo-benzoic acid ethyl ester (19.3 g, 84 mmol), 2,5-bis-tributylstannanyl-thieno[3,2-b]thiophene (20.2 g, 28 mmol) and anhydrous N,N-dimethylformamide (200 cm3) is degassed by nitrogen for 30 minutes. To the mixture is added bis(triphenylphosphine) palladium(II) chloride (990 mg, 1.4 mmol) and the mixture further degassed for 5 The mixture is then heated at 100 C. for 17 hours. After cooling, the mixture is poured into water (500 cm3), extracted with dichloromethane (3×300 cm3) and the combined organics dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. The crude product is purified by column chromatography (gradient from 40-60 petrol to dichloromethane) to give 1,1?-diethyl ester 2,2?-thieno[3,2-b]thiophene-2,5-diylbis-benzoic acid (9.44 g, 76%). MS (m/e): 436 (M+, 100%).

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

Reference:
Patent; MERCK PATENT GMBH; Mitchell, William; D’Lavari, Mansoor; Wang, Changsheng; Tierney, Steven; Sparrowe, David; (59 pag.)US9695190; (2017); B2;,
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Adding a certain compound to certain chemical reactions, such as: 1190-39-2, name is malonic acid dibutyl ester, 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 1190-39-2, Formula: C11H20O4

General procedure: According to the literature procedure,10e a 250 mL, two-necked, round-bottomed flask was charged with diethyl malonate (40.0 mmol), water (40.0 mmol), and ethanol (45 mL), the mixture was stirred in 40 C oil bath for 2 h. After that, a solution of potassium tert-butoxide (40.0 mmol) in ethanol (45 mL) was added slowly over 30 min. After completion of addition, the reaction mixture was stirred in 40 C oil bath until consumption of the starting material (monitored by GC analysis). After removing the ethanol solvent by slow evaporation on rotary evaporator, 20 ml diethyl ether was added. The resulting solid was collected by filtration, washed sequentially with 1:1 mixture of diethyl ether and ethanol (5 mL×2) and diethyl ether (10 mL×3), transferred to a round-bottomed flask and dried under vacuum at 50 C for 10 h to provide ethyl potassium malonate in 85% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, malonic acid dibutyl ester, and friends who are interested can also refer to it.

Reference:
Article; Feng, Yi-Si; Wu, Wei; Xu, Zhong-Qiu; Li, Yan; Li, Ming; Xu, Hua-Jian; Tetrahedron; vol. 68; 9; (2012); p. 2113 – 2120;,
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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. 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 3-(4-bromophenyl)propanoate

To a 8 mL sealed tube was added (1S,4S,5R)-5-[[l-cyclopropyl-4-(2,6-dichlorophenyl)- 1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptane 41g (150 mg, 0.40 mmol, 1.00 equiv.), a solution of methyl 3-(4-bromophenyl)propanoate (116 mg, 0.48 mmol, 1.20 equiv.) in toluene (3 mL), Ru-phos (38 mg, 0.08 mmol, 0.20 equiv.), Ru-phos-precatalyst (68 mg, 0.08 mmol, 0.20 equiv.), and Cs2CO3 (260 mg, 0.80 mmol, 2.00 equiv.). The resulting mixture was heated at 110C overnight. Upon cooling to room temperature, the mixture was diluted with EA (50 mL), washed successively with H2O (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1 :3) to give methyl 3-[4-[(1S,4S,5R)-5-[[l- cyclopropyl-4-(2,6-dichlorophenyl)-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptan-2- yl]phenyl]propanoate 43a (108 mg, 50%) as a colorless oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 75567-84-9.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
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Electric Literature of 39149-80-9, A common heterocyclic compound, 39149-80-9, name is tert-Butyl 2-bromopropanoate, molecular formula is C7H13BrO2, 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.

To a stirred solution 9.5 g (0.10 mol) of 2-hydroxypyridine in 250 mL of DMF was added 16.6 g (0.120 mol) of potassium carbonate followed by 25.0 g (0.120 mol) of 2- bromopropionic acid fert-butyl ester. The resulting mixture was stirred at ambient temperature for 7 h then diluted with IL of water. The aqueous phase was extracted with ethyl acetate (3 x 200 mL) and the combined organics were washed with water (2 x 100 mL), brine (100 mL), dried over magnesium sulfate, filtered and evaporated in vacuo. The crude residue was purified by silica gel chromatography eluting with 25% ethyl acetate in hexanes to afford the title compound as a clear gum 16 g (72%). LC-MS: m/z (ES) 224 (MH)+

The synthetic route of 39149-80-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/123870; (2009); A1;,
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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. 150726-89-9, name is Dimethyl 2-(2-methoxyphenoxy)malonate, This compound has unique chemical properties. The synthetic route is as follows., name: Dimethyl 2-(2-methoxyphenoxy)malonate

a) At 5 C. 12.7 g of sodium methylate was added portionwise to a solution of 18.9 g of dimethyl-2-(o-methoxyphenoxy)malonate in 450 ml of methanol. Upon completion of the addition stirring was continued at room temperature for 30 min followed by the addition of 6 g of formamidine hydrochloride. The mixture was stirred at room temperature for 72 h. Eventually, the solvent was removed under reduced pressure and the remaining residue was suspended in diethyl ether. The solid material was filtered off and dissolved in 100 ml of water. The solution was acidified with conc. hydrochloric acid. A white precipitate formed. The precipitate was collected, washed with water and dried to give 15.1 g of 5-(o-methoxyphenoxy)-4,6-dihydroxy-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; Actelio Pharmaceuticals Ltd.; US6596719; (2003); B1;,
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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. 10203-58-4, name is Diethyl isobutylmalonate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 10203-58-4

EXAMPLE 2 Preparation of 2-ethoxycarbonyl-4-methylvaleric acid A mixture of potassium hydroxide at 85% (3.6 g; 57.34 moles), water (10 ml) and ethanol (10 ml) was heated at 70 C. and hence ethyl 2-ethoxycarbonyl-4-methylvalerate (11.75 g; 54.34 mmoles), prepared as described in example 1, was therein added. After keeping the reaction mixture at reflux temperature for 2 hours, ethanol was evaporated and the resultant solution was washed with ethyl acetate and acidified with concentrated hydrochloric acid. After extracting with ethyl acetate, drying and evaporating the solvent at reduced pressure, 2-ethoxycarbonyl-4-methylvaleric acid (6.7 g; 65.5% yield) was obtained as a colorless oil. 1 H-NMR (200 MHz, CDCl3): delta (ppm): 0.90 (d, 6H); 1.25 (t, 3H); 1.60 (m, 1H); 1.79 (t, 2H); 3.44 (t, 1H); 4.19 (g, 2H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 10203-58-4.

Reference:
Patent; Zambon Group S.p.A.; US5739123; (1998); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 116419-94-4, 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. 116419-94-4, name is Methyl 4-methyl-3-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 4-(bromomethyl)-3-(trifluoromethyl) benzoic acid: Methyl 4-methyl-3-(trifluoromethyl)benzoate (4.0 g, 18.3 mmol) in CCL, (40 mL) with NBS (3.9 g, 22 mmol) and benzoylperoxide with 25% of water (0.55 g, 1.7 mmol) were stirred and heated to reflux for 6 h. Solvent was evaporated, a water solution of K2CO3 was added and product is extracted with EtOAc to obtain a pale yellow solid (7.64 g, 25.7 mmol). Yield = 140% (crude).

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

Reference:
Patent; ORIBASE PHARMA; CHEVE, Gwenael; DAYDE-CAZALS, Benedicte; FAUVEL, Benedicte; BORIES, Cedric; YASRI, Abdelaziz; WO2014/102377; (2014); A1;,
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Synthetic Route of 6091-64-1, 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. 6091-64-1, name is Ethyl 2-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-bromobenzoicacid ethyl ester 22 (1.5g, 6.6mmol) was dissolved in 15mL of ethanol, then under ice-cooling was slowly added dropwise with hydrazine hydrate (1.3g, 26mmol), after the addition was complete, it was stirred at room temperature for 15min, then heated under reflux for 10h. After completion of the reaction, ethanol was removed by rotary evaporation, poured into water, extracted with ethyl acetate, the organic phase was dried and concentrated to give the desired product 23 (1.2g, 86%), without purification into the next step.

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

Reference:
Patent; Jiangshu Alpha Biopharmaceuticals, Inc.; Jiangnan University; Nanjing Drum Tower Hospital; Feng, Bainian; Yang, Guijun; Tang, Chunlei; Wang, Guping; Jie, Desheng; (36 pag.)CN105481765; (2016); A;,
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These common heterocyclic compound, 57267-03-5, name is Ethyl 2,2,2-triethoxyacetate, 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. name: Ethyl 2,2,2-triethoxyacetate

To a solution of 2M LDA in THF/hexane/ethylbenzene (4.3 ml, 8.60 mmol) in dry THF (5 ml) cooled to -78C under inert atmosphere was added methylpyrazine (0.40 g, 4.25 mmol). The RM was stirred for 15 min then ethyl 2,2,2-triethoxyacetate (1.03 ml, 4.68 mmol) was added. The solution was allowed to warm to RT and stirred for 16 h. The RM was poured into 1M HC1 and stirred for 1 h. The mixture was neutralized with NaHC03 solution and extracted three times with DCM. The combined organics were washed with brine, dried over Na2S04, filtered and evaporated. The crude was purified by FCC (0 – 90 % EtOAc in DCM) to give the title compound as an orange solid. Y = 87 %. NMR (300 MHz, chloroform-) delta 13.01 (s, 1H), 8.60 (d, J= 2 Hz, 1H), 8.49 (d, J= 3 Hz, 1H), 8.45 – 8.41 (m, 1H), 6.66 (s, 1H), 4.40 (q, J= 7 Hz, 2H), 1.42 (t, J= 7 Hz, 3H)

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

Reference:
Patent; NODTHERA LIMITED; BOCK, Mark G.; WATT, Alan Paul; PORTER, Roderick Alan; HARRISON, David; (229 pag.)WO2019/25467; (2019); A1;,
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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. 773873-90-8, name is Methyl 5-fluoro-2-(trifluoromethyl)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 5-fluoro-2-(trifluoromethyl)benzoate

Example 15a) 5-Dimethylamino-2-trifluoromethyl-benzoic acid methyl ester (15a)To a stirred solution of 4,48 g (22.5 mmol) 5-Fluoro-2-trifluoromethyl-benzoic acid methyl ester (Rarechem) and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 8h at 600C in an autoclave and was reduced with high vacuum rotation evaporator at 650C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude was purified by column chromatography and the desired product 15a was obtained in 72 % yield (4,00 g, 16,2 mmol).MS-ESI: 248 (M+ +1 , 100). Elementary analysis: C 53.44% H 4.89% F 23.05% N 5.67% Determined: C 53.45% H 4.90% F 23,05% N 5.65%

The synthetic route of 773873-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2008/28688; (2008); A2;,
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