Month: July 2021

Adding a certain compound to certain chemical reactions, such as: 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate, 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 87808-49-9, HPLC of Formula: C9H9BrO2

Methyl 2-bromo-4-methylbenzoate (0.0573 g, 0.25 mmol), alpha-methylstyrene (0.065 mL, 0.50 mmol), palladium acetate (0.0056 g, 0.025 mmol),Tris(4-trifluoromethylphenyl)phosphine (0.0233 g, 0.05 mmol), silver carbonate (0.1379 g, 0.5 mmol), p-toluenesulfonic acid monohydrate (0.0048 g, 0.025 mmol), 1,1,1,3 3,3-Hexafluoro-2-propanol (0.5 mL), o-xylene (0.5 mL), stirred uniformly in a clean and dry closed reaction tube, and then heated to 130 C for 12 hours.After completion of the reaction, the reaction tube was cooled to room temperature, and the reaction system was diluted with 30 mL of ethyl acetate and transferred to a 100 mL separatory funnel. 20 mL of a saturated aqueous solution of ammonium chloride was added thereto, shaken, and allowed to stand to remove the aqueous phase of the lower layer. After that, 20 mL of saturated brine was added thereto, and the mixture was shaken, and the mixture was allowed to stand. The lower aqueous layer was removed, the organic phase was dried over anhydrous sodium sulfate, and the solvent was evaporated. =20:1-10:1, v/v) Separate and purify, remove the solvent by rotary distillation, and drain the oil to obtain a colorless oil.The target product was 56.6 mg, yield 90%.

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; Shanxi University; Wen Zhenkang; Ge Xiaomin; Liu Yufang; Chao Jianbin; (16 pag.)CN108774206; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

107317-58-8, name is Methyl 4-bromo-3-(trifluoromethyl)benzoate, 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. category: esters-buliding-blocks

General procedure: A suspension of 4-(((lS,4S,5R)-2-azabicyclo[2.2.1]heptan-5-yoxy)methy)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole hydroiodide salt l2dd (0.52 mrnol, 1 equiv.),methyl4-bromo-2/3-substituted benzoate 106-y (0 68 mmol, 1.3 equiv.), Cs2C03 (1.3 mmol,15 2.5 equiv.), Pd?(dha)3 (0.15 equiv.), BINAP (0.2 equiv.) in Toluene (10.0 mL) was heatedunder a nitrogen atmosphere at 1 J 0C for 16 h. The reaction rnixture was cooled to roomtemperature, diluted with ethyl acetate and filtered through a pad ofCelite. The organic layerwas washed with brine, dried over anhydrous Na2S04, filtered and concentrated 1..mderreduced pressure. The crude material v.·as purified on ISCO silica gel column20 chromatography using hexane/ethyl acetate as eluents to give the desired methyl ester l06zwhich was used as such in the next step.

The synthetic route of 107317-58-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 26218-04-2,Some common heterocyclic compound, 26218-04-2, name is 2-Ethylhexyl 4-aminobenzoate, molecular formula is C15H23NO2, 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.

A mixture of 2, 4-dichloro-6- (l-methyl-lH-pyrazol-5- yl) -1, 3, 5-triazine (0.23 g, 1 mmol) , 2-ethylhexyl 4- aminobenzoate (0.50 g, 2 mmol) and potassium carbonate(0.30 g, 2.17 mmol) in dioxane (15 mL) is heated to 900C for 4 hours following the reaction by TLC. The solvent is evaporated at low pressure, the residue is diluted in methylene chloride and the organic phase is washed with water. The solvent is removed at low pressure and the resulting crude product is purified by silica gel chromatography to yield 2, 4-bis{4- [ (2- ethylhexyloxy) carbonyl]phenylamino}-6- (1-methyl-lH- pyrazol-5-yl) -1, 3, 5-triazine (0.56 g, 0.85 mmol, 85%, thick oil) .1H RMN (300 MHz, DMSO-d6) : delta 0.82-0.94 (m, 12H), 1.23- 1.46 (m, 16H), 1.67 (m, 2H), 4.17 (d, J= 4.4 Hz, 4H), 4.30 (s, 3H), 7.06 (br s, IH), 7.54 (d, J= 1.9 Hz, IH), 7.94 (br s, 8H), 10.29 (br s, 2H) .UV lambdamax= 293 nm epsilon= 59000 M’1 cm”1 (methanol) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Ethylhexyl 4-aminobenzoate, its application will become more common.

Reference:
Patent; ISDIN, S.A.; WO2006/64366; (2006); A1;,
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. 18358-63-9, name is Methyl 4-(methylamino)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 4-(methylamino)benzoate

The compound (3.1 g, 18.6 mmol) obtained in Step 4 above was dissolved in THF (37 mL). A solution prepared by dissolving LiAlH4 in THF (9.3 mL, 18.6 mmol) was slowly added thereto at 0 C. The resulting mixture was stirred for 8 hrs at 0 C, and an aqueous solution of Na2S04 was added to complete the reaction. Subsequently, a saturated aqueous solution of HC1 (50 mL) was added thereto, and the resulting mixture was stirred for 1 hr to form two different layers. The aqueous layer was extracted with EtOAc, and the organic layer was dried over Na2S04, distilled under reduced pressure, and purified by column chromatography (EtOAc/Hexane = 1/1 (v/v)) to obtain the title compound (1.4 g, 54%). 1H NMR (CDC13, 400 MHz) delta 7.21 (d, 2H), 6.61 (d, 2H), 4.56 (s, 2H), 2.85 (s, 3H)

The synthetic route of 18358-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; KIM, Dong Jin; YOO, Kyung Ho; KIM, Young Soo; PARK, Woong Seo; KANG, Yong Koo; KIM, Hye Yun; KIM, Yun Kyung; PARK, Ki Duk; KIM, Maeng Sup; SUH, Kwee Hyun; AHN, Young Gil; WO2013/147568; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 139102-34-4, 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 139102-34-4 as follows.

[00197] Step 1: A mixture of methyl 4-bromo-2-methoxybenzoate (2.66 g, 10.85 mmol), 28% ammonium hydroxide (25 mL, 642 mmol) and ammonium chloride (2.0 g, 37.4 mmol) was stirred at RT for 20 min and then at 50 0C. Once the material converted forms to an oil (ca. 20 min), the mixture was cooled to RT and more ammonium hydroxide (25 mL, 642 mmol) and ammonium chloride (2.0 g, 37.4 mmol) were added. Upon completion of addition, the reaction mixture was stirred at RT overnight. After this time, the mixture was heated to reflux in an open flask to drive off the excess ammonia and then cooled to RT. The mixture was neutralized with cone. HCl and then extracted with ethyl acetate. The extract was dried (Na2SO4) and then concentrated to give a residue. The residue was purified by flash chromatography (40 g silica gel cartridge; EtO Ac/Hex) to give 4-bromo-2- methoxybenzamide (510 mg, 2.22 mmol, 20 % yield) as a white solid.

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:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CARTER, Percy H.; CORNELIUS, Lyndon A., M.; WO2008/42925; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 10601-80-6, 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 10601-80-6 as follows.

Tin (II) chloride dihydrate (9.026 g, 40.0 mmol) was added to a solution of 4-bromo-2-nitrobenzaldehyde (2.3 g, 10.0 mmol) and EtOH (40 ml) followed by 3,3-diethoxypropionic acid ethyl ester (4.75 g, 25.0 mmol ). The reaction was heated to 90 oc for4 hr upon the cooling, the reaction mixture was concentrated and the residue was dissolved inEtOAc and quenched with sat. NaHC03. The resulting emulsion was filtered through a pad ofcelite and rinsed well with EtOAc. The remaining aqueous layer was extracted with EtOAcand the combined organic layer were washed with brine, dried over Na2S04 andconcentrated. The crude product was purified by silica gel column chromatography with 10-30% ofEtOAc in hexanes to give ethyl 7-bromoquinoline-3-carboxylate (0.6 g, 21.5%). OH(400 MHz; CDCh) 1.47 (3H, t, J= 8.0 Hz), 4.50 (2H, q, J= 8.0 Hz), 7.72 (1H, t, J= 4.0 Hz),7.80 (1H, s), 8.36 (1H,s), 8.82 (1H, s), 9.45 (1H, s). 8c (100 MHz; CDCh) 14.3, 61.7, 123.5,125.4,126.3, 130.2, 131.1, 138.5, 150.2, 151.0, 165.0.

According to the analysis of related databases, 10601-80-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; UNIVERSITY OF KANSAS; HE, John Cijiang; LIU, Ruijie; DAS, Bhaskar; XIAO, Wenzhen; LI, Zhengzhe; LEE, Kyung; (32 pag.)WO2018/129274; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, 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. Quality Control of Methyl 2-(4-bromophenyl)-2,2-dimethylacetate

Methyl 2-(4-bromophenyl)-2-methylpropanoate (689 mg, 2.68 mmol),(R)-3-oxo hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylic acid tert-butyl ester (630 mg, 2.61 mmol),Pd2(dba)3 (180 mg, 0.19 mmol),2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (550 mg, 1.26 mmol),Cs2CO3 (173 mg, 0.53 mmol) and1,4-dioxane (25mL)Add to a 50mL two-neck bottle,The reaction mixture was reacted under nitrogen for 12 h at 90 C.After the reaction was completed, the reaction was cooled to EtOAc. Add EtOAc (75 mL) and water to the filtrate(50 mL), the resulting mixture was shaken and layered. The aqueous phase was extracted with EtOAc (50 mL).Filtration and concentrating the filtrate under reduced pressure, and the obtained residue was purified by silica gel column chromatography (PE/EA (V/V)=1.2/1)The product was a white solid (200mg, 17.88%)

The synthetic route of Methyl 2-(4-bromophenyl)-2,2-dimethylacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Xinchang; Ren Qingyun; Yan Guanghua; S ·geerdeman; Zhang Yingjun; (200 pag.)CN109678859; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 4630-80-2, 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. 4630-80-2, name is Methyl cyclopentanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Synthesis of methyl 1-methylcyclopentanecarboxylate:To a solution of di-isopropylamine (69 ml) in tetrahydrafuran (100 ml), n- BuLi (166 ml) in hexane was added at 0 C and the reaction mixture was allowed to stir at same temperature for about 10-15 minutes. The reaction mixture was stirred at room temperature for about 45 minutes. Methyl cyclopentanecarboxylate (25 g) in tetrahydrafuran (200 ml) was added drop-wise at -78 C to above reaction mixture. The reaction mixture was stirred at same temperature for about 2 hours and then methyl iodide was added drop-wise. The reaction was maintained at -78C for an hour and allowed to attain room temperature. The reaction mixture was stirred overnight at room temperature and quenched at 0 C with saturated aq. NH4C1 solution and the compound was extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over anhydrous Na2S04 and concentrated. Crude product was directly used for the next step. 1H NMR (CDC13, 300 MHz): 3.66 (s, 3H), 2.10- 2.03 (m, 2H), 1.69- 1.64 (m, 4H), 1.50- 1.42 (m, 2H), 1.23 (s, 3H).

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

Reference:
Patent; HETERO RESEARCH FOUNDATION; PARTHASARADHI REDDY, Bandi; MANOHAR SHARMA, Vedula; RATHNAKAR REDDY, Kura; VL SUBRAHMANYAM, Lanka; SUDHAKAR, Neela; WO2012/25857; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 145576-28-9, name is Ethyl 4-methylenecyclohexanecarboxylate, 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 145576-28-9, COA of Formula: C10H16O2

General procedure: The alkene (1.16 mmol, 1 equivalent) was dissolved in a vigorously stirred mixture of DCM (7 mL) and acetonitrile (7 mL) under nitrogen. 2,6-Lutidine (0.27 mL, 2.32 mmol, 2 equivalents), water (10.5 mL) and sodium periodate (993 mg, 4.64 mmol, 4 equivalents) were then added sequentially. The reaction concentration with respect to the alkene was 0.047 M in a mixture of 1: 1: 1.5 – DCM: acetonitrile: water. To the resulting mixture a stock solution of ruthenium(III) chloride trihydrate (0.035 M in water) (1.16 mL, 0.04 mmol, 3.5 mol %) was added dropwise via a syringe forming a brown suspension. The reaction was stirred vigorously at 20 C for 1 h (or for the time indicated in the Tables 2 and 3). The reaction was diluted with water (20 mL) then extracted with DCM (3 x 20 mL). The organic extracts were combined then washed with brine (20 mL), passed through a phase separating cartridge and the volatiles were removed under reduced pressure. The resulting residue was purified by flash silica chromatography (EtOAc / heptane) to afford the ketone.

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:
Article; Watson, David W.; Gill, Matthew; Kemmitt, Paul; Lamont, Scott G.; Popescu, Mihai V.; Simpson, Iain; Tetrahedron Letters; vol. 59; 51; (2018); p. 4479 – 4482;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 33491-30-4, 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. 33491-30-4 name is 8-Bromo-2H-chromen-2-one, 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.

(3) Weigh 1.8g of Br-C8 (8.89mmol),0.28 g of Pd(PPh3)4 (0.24 mmol) in a SCHLENK reaction tube under N2 atmosphere,35 mL of toluene was added, and 3.53 g of tri-n-butyl 2-pyridinium (9.60 mmol) was added dropwise.The reaction was stirred at 110 C for 16 h. After completion of the reaction, the mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure.It was separated and purified by silica gel column chromatography, and the mobile phase was dichloromethane.Finally, L-C8 was obtained as a white solid 1.49 g, and the yield was 83.2%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Bromo-2H-chromen-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Xi’an Jiaotong University; Zhou Guijiang; Feng Zhao; Yang Xiaolong; (40 pag.)CN109608502; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics