Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 541-16-2, name is Di-tert-Butyl malonate, 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 541-16-2, Safety of Di-tert-Butyl malonate

Step 1: Preparation of 2-ethylcyclopropane-1,1-dicarboxylic acid di-tert-butyl ester, shown below To a suspension of benzyltriethylammonium chloride (21.0 g, 92.2 mmol) in a 50% aqueous NaOH solution (92.4 g in 185 mL H2O) was added 1,2-dibromobutane (30.0 g, 138.9 mmol) and di-tert-butylmalonate (20.0 g, 92.5 mmol). The reaction mixture was vigorously stirred for 18 hours at room temperature and treated with a mixture of ice and water. The crude product was extracted with dichloromethane (3*) and sequentially washed with water (3*), and brine. The organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was purified by flash column chromatography (100 g SiO2, 3% diethyl ether in hexane) to provide the desired product (18.3 g, 67.8 mmol, 73% yield) which was used directly in the next reaction.

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, Di-tert-Butyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/274648; (2009); 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 148547-19-7 as follows. category: esters-buliding-blocks

The compound 120a (1.0 g, 4.365 mmol) was dissolved in 1,4-dioxane (30 mL), and the compound 120b (2.22 g, 8.73 mmol), KOAc (1.5 g, 15.277 mmol), and PdCl2 were added. (dppf) (0.32 g, 0.436 mmol) and,Nitrogen was replaced three times, and then the reaction solution was stirred at 95 C for 16 hours. Cool to room temperature, add water (60 mL),Extracted with ethyl acetate (30 mL x 3), combined the organic layers and washed with water (30 mL x 2), dried over MgSO4, filtered and concentrated,The concentrate was purified by silica gel chromatography (ethyl acetate: petroleum ether = 0-10%) to obtain a white off-white compound 120c, 3-methyl-4- (4,4,5,5-tetramethyl-1, Methyl 3,2-dioxaborolan-2-yl) benzoate (1.113 g, yield 92.4%).

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiaxing Tekeluo Biological Technology Co., Ltd.; Xing Li; Li Guanqun; Wang Xiaolei; Cai Yuting; Jiang Xiang; Pan Xiang; Zhu Wenhao; Wang Yang; Wang Zengquan; (83 pag.)CN110627775; (2019); A;,
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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. 1187318-53-1, name is 3-Bromo-5-fluoro-2-methyl-benzoic acid methyl ester, A new synthetic method of this compound is introduced below., name: 3-Bromo-5-fluoro-2-methyl-benzoic acid methyl ester

To a solution of methyl 3-bromo-5-fluoro-2-methylbenzoate (3.38 g, 13.7 mmol) in CCl4 (40 mL) at RT was added NBS (3.18 g, 17.9 mmol) and the reaction flask was purged with N2. After heating at 85 C for 5 m, AIBN (1.18 g, 6.87 mmol) was added, and the mixture was heated at 85 C overnight. The mixture was concentrated, diluted with H2O, and extracted with EtOAc. The organic phase was dried over Na2S04, filtered, and concentrated to give the crude product, which was purified using silica gel eluting with EtOAc in petroleum ether (0% to 1%) to give methyl 3-bromo-2-(bromomethyl)-5-fluorobenzoate (3.3 g, 74% yield) as an oil.

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; BIOTHERYX, INC.; CHAN, Kyle W.H.; CHOURASIA, Aparajita Hoskote; FUNG, Leah; MERCURIO, Frank; SULLIVAN, Robert; (0 pag.)WO2019/173224; (2019); A1;,
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Application of 3196-23-4, 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. 3196-23-4 name is Methyl 1-bromocyclohexanecarboxylate, 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.

General procedure: A mixture of 2.5 g of zinc, 5.53 g (25 mmol) of bromo ester 1, a catalytic amount (5 mg) of HgCl2, and 40 mL of benzene was heated for 3 h under reflux. The mixture was cooled, 10 mmol of aldehyde 4a-4i was added, and the mixture was heated for 2 h under reflux.After cooling, the mixture was treated with 5% aqueous acetic acid, the organic phase was separated and dried over Na2SO4, and the solvent was distilled off.The crystalline product (7a-7i) was recrystallized from ethyl acetate. Treatment of the residue with methanol led to crystallization of compound 11a-11d which was recrystallized from methanol.

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

Reference:
Article; Kirillov; Nikiforova; Vasyanin; Dmitriev; Russian Journal of Organic Chemistry; vol. 51; 4; (2015); p. 513 – 517; Zhurnal Organicheskoi Khimii; vol. 51; (2015); p. 530 – 534,5;,
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Some common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, molecular formula is C8H15BrO2, 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. Product Details of 110661-91-1

Under a N2 atmosphere, NaH (219 mg, 5.99 mmol, 60% dispersion in mineral oil) was added to a stirring suspension of fert-butyl 3-oxopiperazine-l-carboxylate (1 g, 4.99 mmol) in THF (20 mL) at 0C and stirred for five minutes. Ethyl 4-bromobutanoate (1.33 g, 5.99 mmol) was added at 0C. The reaction was stirred overnight. The reaction was quenched with several drops of methanol, diluted with ethyl acetate, and washed with H20, brine, and dried over magnesium sulfate. The organic layer was concentrated in vacuo which provided the crude material as a clear oil. The crude oil was purified by flash chromatography with ethyl acetate in hexanes as the eluent to afford Intermediate 23A (364 mg, 21%) as a clear oil. LCMS (method A): m/z 343.4 (M+H)+. lH NMR (CDC13): delta 4.06 (s, 2H), 3.63 (t, 2H), 3.42 (t, 2H), 3.36 (t, 2H), 2.26 (t, 2H), 1.84 (quin, 2H), 1.46 (s, 9H), 1.44 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 110661-91-1, its application will become more common.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; MCGUINNESS, Brian F; XU, Xiaoqing; KULTGEN, Steven G.; MCMASTER, Ellen Sieber; BEASLEY, James R.; (356 pag.)WO2018/5794; (2018); A2;,
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Related Products of 6279-86-3, The chemical industry reduces the impact on the environment during synthesis 6279-86-3, name is Triethyl methanetricarboxylate, I believe this compound will play a more active role in future production and life.

p-Methoxyaniline (123 mg, 1 mmol) was dissolved in dimethylformamide (1 ml).;Then, triethyl methanetricarboxylate (232 mg, 1 mmol) was added.;The mixture was heated for six hours at 170-190 C. The reaction was cooled to rt and treated with ethanol, filtered and washed with ethanol to yield 8 as a yellow solid (143 mg, 58%); mp 308-310 C; 1H NMR (500 MHz, DMSO-d6) delta 3.79 (s, 3H), 3.86 (s, 3H), 7.01 (d, J = 8.9 Hz, 2H), 7.40 (br s, 3H), 7.59 (d, J = 8.9 Hz, 2H), 12.01 (s, 1H), 12.63 (s, 1H), 16.67 (s, 1H); 13C NMR (125.7 MHz, DMSO-d6) delta 55.09, 55.38, 96.39, 104.22, 114.13, 114.51, 117.33, 122.13, 123.65, 129.58, 133.11, 154.53, 156.26, 161.98, 168.39, 171.37; Anal. for C18H16N2O5: Calcd C, 63.52; H, 4.74; N, 8.23. Found C, 63.66; H, 5.00; N, 8.09.

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, Triethyl methanetricarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sabbah, Dima A.; Simms, Neka A.; Wang, Wang; Dong, Yuxiang; Ezell, Edward L.; Brattain, Michael G.; Vennerstrom, Jonathan L.; Zhong, Haizhen A.; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7175 – 7183;,
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Ester – an overview | ScienceDirect Topics

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. 110661-91-1, name is tert-Butyl 4-bromobutanoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H15BrO2

Exemplification of General Procedure J:; Preparation of teri-butyl 4-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)-l/7- indol-l-yl)butanoate; To a solution of 3-(3-chloro-4-isopropoxyphenyl)-5-(lH-indol-4-yl)-l,2,4-oxadiazole (0.100 g, 0.283 mmol) in DMF (0.999 mL) was added NaH (0.012 g, 0.311 mmol). After about 15 min tert- butyl 4-bromobutanoate (0.095 g, 0.424 mmol) was added and the reaction mixture was heated to about 50 C. After about 24 h the reaction mixture was cooled to ambient temperature, concentrated in vacuo and purified by chromatography on silica gel (eluting with EtOAc/Hep) to provide tert-butyl 4-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)-lH-indol-l- yljbutanoate (0.135 g, 93%) as a colorless oil that solidified on standing. LC/MS (Table 1, Method c) Rt = 3.50 min, m/z 496 (M+H)+.

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

Reference:
Patent; ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R.; WO2011/71570; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 39149-80-9, name is tert-Butyl 2-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H13BrO2

General procedure: BuLi (1.6 M in hexane, 1.45 equiv) was added to a stirred solution of 3 in THF (0.022 M) at -78 C and the resultant mixture was stirred at -78 C for 1 h. The requisite electrophile was added and the resultant mixture was stirred at -78 C for 10 min, then MeOH was added. The reaction mixture was concentrated in vacuo and the residue was extracted with CH2Cl2, then filtered through basic alumina (grade V) and purified by flash column chromatography on basic alumina (grade I) to give 28-30.

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 39149-80-9.

Reference:
Article; Bashiardes, George; Bodwell, Graham J.; Collingwood, Stephen P.; Costello, James F.; Davies, Stephen G.; Fletcher, Ai M.; Garner, Alan; Preston, Simon C.; Thomson, James E.; Tetrahedron; vol. 70; 46; (2014); p. 8938 – 8951;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 148547-19-7, name is Methyl 4-bromo-3-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 148547-19-7, Formula: C9H9BrO2

A suspension of methyl 4-bromo-3-methylbenzoate (ABCR AV19078; 3 g; 13.10 mmol; 1 eq.), 2-(trifluoromethyl)phenylboronic acid (Aldrich 393606; 2.74 g; 14.41 mmol; 1.10 eq.), potassium carbonate (9.05 g; 65.48 mmol; 5 eq.) and tetrakis(triphenylphosphine)palladium(0) (1.51 g; 1.31 mmol; 0.10 eq.) in toluene (15 ml_) and water (15 ml_) was refluxed for 3 hours. The resulting mixture was filtered through a short pad of Celite, which was further washed with toluene. After evaporation of the solvent, the residue was taken up in ethyl acetate and washed successively with sat. aq. NaHCC>3, water and brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (3.7 g, 96%) as a brown oil. HPLC (Method A) : Rt 5.34 min (purity 70.9%). LC/MS : 294.9 (M+H)+.

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; MERCK SERONO S.A.; WO2009/43890; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 55666-43-8, 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. 55666-43-8, name is tert-Butyl 3-bromopropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 350mg (1. 44mmol) of 2- (2, 4-dichlorophenoxy) ethanamine and 0. 2ml (1. 44mmol) of triethylamine in 30ml of [DICHLOROMETHANE] stirring at room temperature under a nitrogen atmosphere was added 0. 21 ml (1. 44mmol) aliquots, every 30 minutes, of tert-butyl bromoacetate until the starting material was completely consumed. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with [DICHLOROMETHANE] : methanol : ammonia (95: 5: 0.5) to give the title compound (300mg, 65%) as a colourless oil. ‘H-NMR [(400MHZ,] [CDC13)] [A] = 1.42-1. 45 (s, 9H), 3.03-3. 07 (t, 2H), 3.59 (s, 2H), 4.08- 4.12 (t, [2H),] 6.83-6. 88 (d, [1H),] 7.14-7. 18 (m, [1H),] 7.34-7. 37 (m, [1H).]

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

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/16583; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics