Tag: M.W=200-300

Some common heterocyclic compound, 57381-43-8, name is Methyl 2,5-dibromobenzoate, molecular formula is C8H6Br2O2, 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. 57381-43-8

General procedure: A mixture of magnesium turnings (0.036g, 1.5mmol), bromobenzene (0.15g, 1mmol), tri-n-butyltin chloride (0.49g, 1.5mmol) and 1,2-dibromoethane (0.094g, 0.5mmol) as initiator in dry THF (5mL) was sonicated for 1h in an ultrasonic cleaning bath at around 35¡ãC, with monitoring of the reaction by TLC. Once the reaction finished, aqueous saturated NH4Cl solution (40mL) was added and extracted with ethyl acetate (3¡Á20mL). The combined extracts were washed with brine (60mL) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the product was isolated by column chromatography with silica gel doped with 10percent of KF to retain tri-n-butyltin halides formed during the reaction. 4 (0.286, 0.78mmol, 78percent) eluted with 98:2 (hexane/diethyl ether).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57381-43-8, its application will become more common.

Reference:
Article; Gerbino, Dario C.; Fidelibus, Pablo M.; Mandolesi, Sandra D.; Ocampo, Romina A.; Scoccia, Jimena; Podesta, Julio C.; Journal of Organometallic Chemistry; vol. 741-742; 1; (2013); p. 24 – 32;,
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24398-88-7, Adding a certain compound to certain chemical reactions, such as: 24398-88-7, name is Ethyl 3-bromobenzoate, 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 24398-88-7.

The N-(3-amino-4-methylphenyl)-3-morpholinobenzamide used as a starting material was prepared as follows: A mixture of ethyl 3-bromobenzoate (1.92 ml), morpholine (1.25 ml), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.336 g), sodium tert-butoxide (1.615 g) and tris(dibenzylideneacetone)dipalladium(0) (0.33 g) and toluene (25 ml) was stirred and heated to 90 C. for 18 hours under argon. The reaction mixture was allowed to cool to ambient temperature and extracted with 1M hydrochloric acid. The aqueous phase was basified with concentrated sodium hydroxide solution and extracted with ethyl acetate. The organic phase was dried over magnesium sulphate, filtered and evaporated to dryness. The residual oil was purified by column chromatography on silica gel using a 47:3 mixture of methylene chloride and methanol as eluent to yield N-(3-morpholinobenzoyl)morpholine (0.45 g).

According to the analysis of related databases, 24398-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astrazeneca AB; US6593333; (2003); B1;,
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25542-62-5, A common compound: 25542-62-5, name is Ethyl 6-bromohexanoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 9 Synthesis of 3-[3-(5-carboxypentyl)-5-iodo-2,3-dimethyl-3H-1-indoliumyl]-1-propanesulfonate (2) A mixture of 13.4 g (0.12 mol) of potassium tert-butoxide and 100 g of tert-butanol was stirred and heated until the tert-butoxide totally dissolved. The solution was cooled to about 50 C. and 17 g (0.12 mmol) of ethyl 2-methylacetoacetate was added dropwise. Ethyl-6-bromohexanoate (30 g, 0.13 mmol) was then added dropwise and the reaction mixture was stirred and refluxed for 5 hours. The mixture was filtered and the solvent was removed under reduced pressure. The residue was partitioned between 1M HCl and chloroform. The organic layer was dried over magnesium sulfate and purified on silica gel using 1:10 ethyl acetate/hexane as the eluent to yield 25 g (75%) of diethyl 2-acetyl-2-methyloctanedioate (3) as yellow liquid.

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 6-bromohexanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NANOQUANTUM SCIENCES, INC.; Jones, Gary W.; Tatarets, Anatoliy L.; Patsenker, Leonid D.; US2013/231604; (2013); A1;,
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139102-34-4, 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. 139102-34-4, name is Methyl 4-bromo-2-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

L1BH4 (0.66 g) was added portion- wise to a solution of methyl 4-bromo-2- methoxybenzoate (5 g) in dry THF (50 mL) and EtOH (10 mL) was added. The reaction was stirred for 18h. The mixture was then poured into aq. NaOH (1M, 300 mL) and extracted with EtOAc. The organics were combined, washed with water then sat. brine before being dried (MgS04), and concentrated in vacuo to give the sub-title compound (4.4 g) as a gum; 1H NMR: 7.30 (d, 1H), 7.17-7.11 (m, 2H), 5.10 (t, 1H), 4.43 (d, 2H), 3.79 (s, 3H).

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

Reference:
Patent; ASTRAZENECA AB; DAINIPPON SUMITOMO PHARMA CO., LTD.; ASTRAZENECA UK LIMITED; BAILEY, Andrew; HIGHTON, Adrian John; MCINALLY, Thomas; MOCHEL, Tobias; URABE, Daisuke; WO2012/66335; (2012); A1;,
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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. 94-60-0 name is Dimethyl cyclohexane-1,4-dicarboxylate, 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. 94-60-0

Comparative Examples 1-3Using the same procedure as in Examples 7-9, DMCD was hydrogenated using a commercially available copper chromite catalyst. Analysis of the reactor effluent was carried out by gas chromatography and the results are shown in Table 3 as area %. TABLE 3 DMCD Hydrogenation Using Copper Chromite Catalyst Press: 345 barg Feed Rate: 1500 mL/hour Catalyst: CuCr Comp. Temp Mono- trans cis % cis/trans Example ( C.) DMCD ester CHDM CHDM MeOH Water Imp. Conv Ratio 1 205 19.3 11.2 17.6 20.3 31.0 0.3 0.3 77.4 1.2 2 215 16.4 10.6 24.2 23.0 25.8 0.1 0.1 82.6 1.0 3 225 8.3 6.3 26.7 21.3 36.8 0.3 0.2 90.0 0.8

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dimethyl cyclohexane-1,4-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Eastman Chemical Company; US6919489; (2005); B1;,
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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. 252881-74-6 name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, 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. 252881-74-6

To a solution of tert-butyl 13-amino-4,7,10-trioxadodecanoate (0.80 g, 2.89 mmol) in 30 mL of dioxane with stirring was added 10 mL of HCl (36%).After 0.5 hours,TLC analysis showed the reaction was complete, and the reaction mixture was concentrated,And co-concentrated with ethanol and ethanol / toluene,The title product was obtained as the hydrochloride salt (> 90% purity, 0.640 g, 86% yield) without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, and friends who are interested can also refer to it.

Reference:
Patent; Hangzhou Duo Xi Biological Technology Co., Ltd.; Zhao Luoboyongxin; Huang Yuanyuan; Yang Qingliang; Gai Shun; Ye Hangbo; Xu Yifang; Guo Huihui; Cao Minjun; Li Wenjun; Cai Xiang; Zhou Xiaomai; Xie Hongsheng; Jia Junxiang; Guo Zhixiang; Lin Chen; Yang Yanlei; Ye Zhicang; Qi Tafamingrenqingqiubugongkaixingming; (338 pag.)CN110621673; (2019); A;,
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Related Products of 619-42-1, The chemical industry reduces the impact on the environment during synthesis 619-42-1, name is Methyl 4-bromobenzoate, I believe this compound will play a more active role in future production and life.

Eth nytfime hyisfiane (82.4 g, 0,84 mol) was added dropwise over 10 min under a nitrogen atmosphere to a solution of methyl 4-bromobenzoate (150 g, 0.7 mol), PdC (PPh3)2 (15 g, 0.021 mol) and Cu (13 g, 0.07 mol) in TEA (1.5 L) and the reaction was siirsd at 90 for 30 minutes. Solids were collected by filtration and washed with EtOAc (5 x 500 mL). The filtrate was concentrated under reduced pressure to give a residue, which was distilled under reduced pressure to yield methyl 4-C(trimethylsify) ethynyl) benzoate (INT-12) as an off-white solid (156 g, 96%),

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

Reference:
Patent; ACHAOGEN, INC.; PATTERSON, Brian D.; LU, Qing; AGGEN, James Bradley; DOZZO, Paola; KASAR, Ramesh Annasaheb; LINSELL, Martin Sheringham; KANE, Timothy Robert; GLIEDT, Micah James; HILDEBRANDT, Darin James; MCENROE, Glenn A.; COHEN, Frederick; WO2013/170165; (2013); A1;,
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These common heterocyclic compound, 62451-84-7, name is Methyl 2-(3-(trifluoromethyl)phenyl)acetate, 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. SDS of cas: 62451-84-7

EXAMPLE 98; 4-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide; Step 1: A mixture of (3-trifluoromethyl-phenyl)-acetic acid methyl ester (6.0 g, 25.9 mmol) and N-bromosuccinimide (9.2 g, 51.7 mmol) and a few drops of hydrobromic acid (48% solution) in chloroform (250 mL) was heated under reflux for two days. The reaction mixture was concentrated to dryness, taken up in methylene chloride and loaded onto a column of silica gel. Elution with 5% ethyl acetate/hexanes gave Bromo-(3-trifluoromethyl-phenyl)-acetic acid methyl ester (3.0 g, 39% yield) as colorless oil. The NMR spectrum obtained on the sample is compatible with its structure.

The synthetic route of Methyl 2-(3-(trifluoromethyl)phenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brinkman, John A.; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Guertin, Kevin Richard; Marcopulos, Nicholas; Qi, Lida; Racha, Jagdish Kumar; Sarabu, Ramakanth; Tan, Jenny; Tilley, Jefferson Wright; US2007/270433; (2007); A1;,
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10203-58-4, 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. 10203-58-4, name is Diethyl isobutylmalonate, This compound has unique chemical properties. The synthetic route is as follows.

2-aminotetrahydropyrrolidine hydrochloride (1.33 g, 10 mmoL) was dissolved in 60 mL of anhydrous ethanol, and 1.33 mL of triethylamine was added dropwise with constant stirring, and the reaction was carried out for 10 min at room temperature.A solution of sodium ethoxide (1.36 g, 20 mmoL) in absolute ethanol (20 mL) was added dropwise on an ice bath and allowed to react for 45 min at room temperature after the addition was complete.A solution of diethyl isobutyl malonate (2.16 g, 10 mmoL) in absolute ethanol (20 mL) was added dropwise with constant stirring, and the temperature was raised and refluxed for 15 hours.After TLC tracking, after the reaction was completed, the mixture was filtered by suction and the filtrate was collected. The filtrate was evaporated and the solvent was removed to give a yellow solid.100 mL of water was dissolved and 100 mL of ethyl acetate was extracted three times. Fat-soluble impurities were removed and the aqueous phases were combined.Butanol was extracted and the n-butanol layer was collected, rotary evaporated and the solvent removed to give a pale yellow solid.The trichloromethane was dissolved, suction filtered to remove impurities that were insoluble in chloroform, and the filtrate was collected and spin-dryed to give a white solid as the compound 3-isobutyl-tetrahydropyrrole [1,2-a]pyrimidine-2, 4(1H,3H)-dione.

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; Xi’an Jiaotong University; Guo Zengjun; Li Dandan; Zhang Jie; Zhang Hui; Liu Xia; Li Mengyi; Xi Ke; (13 pag.)CN104693205; (2017); B;,
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