Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 4897-84-1, name is Methyl 4-bromobutanoate, 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 4897-84-1, SDS of cas: 4897-84-1

To a solution of 3-bromophenol (3.44 g, 20.0 mmol) and methyl 4-bromobutanoate (4.32 g, 24.0 mmol) in DMF (20 mL) was added K2co3 (5.52 g, 40.0 mmol). The mixture was stirred at rt for 0.5 h and then heated with stirring at 90 oC for 1 h. After diluting with EtOAc (200 mL), the mixture was washed with water (3 x 50 mL), dried and concentrated. The crude product was purified by silica gel column chromatograph (petroleum/EtOAc = 10:1) to give methyl 4-(3- bromophenoxy)butanoate as a white liquid (5.2 g, yield: 96percent). ESI-MS (M+H) +: 273.1

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Reference:
Patent; BIOGEN MA INC.; HOPKINS, Brian, T.; MA, Bin; PRINCE, Robin; MARX, Isaac; LYSSIKATOS, Joseph, P.; ZHENG, Fengmei; PETERSON, Matthew; PATIENCE, Daniel, B.; (205 pag.)WO2018/191577; (2018); A1;,
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Application of 685892-23-3, 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. 685892-23-3, name is Methyl 2-bromo-6-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 4; 4′-{(R)-1-[(3-Amino-oxetane-3-carbonyl)-amino]-ethyl}-3-chloro-3′-fluoro-biphenyl-2-carboxylic acid methyl ester Step A: 4′-((R)-1-tert-Butoxycarbonylamino-ethyl)-3-chloro-3′-fluoro-biphenyl-2-carboxylic acid methyl ester A mixture of {(R)-1-[2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (600 mg, 1.64 mmol, intermediate 13), methyl 2-bromo-6-chlorobenzoate (430 mg, 1.72 mmol) [CAS 685892-23-3; commercially available], tri-o-tolyl-phosphane (100 mg, 329 mumol), potassium carbonate (568 mg, 4.11 mmol) and palladium(II) acetate (18.4 mg, 82.1 mumol) in THF (20.0 ml) and water (1.18 ml) was stirred at room temperature over night. The reaction mixture was diluted with water and extracted three times with EtOAc. The combined extracts were washed with water and brine, dried with Na2SO4 and concentrated in vacuo. The remaining residue was purified by chromatography (silica gel; DCM/EtOAc 100:0-90:10) and the title compound was obtained as colorless oil (385 mg, 58%). MS: 466.1 [M-H+OAc]-.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-6-chlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aebi, Johannes; Binggeli, Alfred; Hertel, Cornelia; Konkar, Anish Ashok; Kuehne, Holger; Kuhn, Bernd; Maerki, Hans P.; Wang, Haiyan; US2012/165338; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22223-49-0, name is Methyl 2-amino-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 22223-49-0, SDS of cas: 22223-49-0

Step B Preparation of methyl 2-[[(2,2-dimethylhydrazino)carbonyl]amino]-3-methylbenzoate To a solution of the title compound of Step A (25.4 g, 154 mmol) in p-dioxane (500 mL) under a nitrogen atmosphere was added diphosgene (22.3 mL, 184 mmol), followed by triethylamine (25.6 mL, 184 mmol). A white precipitate formed, and the resulting mixture was heated to 60 C. overnight. The mixture was cooled to room temperature and filtered. The precipitate was washed with diethyl ether and the combined filtrates were concentrated under reduced pressure to afford an oil (30.97 g) which, without further characterization, was dissolved in toluene (400 mL). To this solution at 0 C. under a nitrogen atmosphere was added 1,1-dimethylhydrazine (12.3 mL, 162 mmol) and the resulting milky suspension was stirred at 0 C. for 30 min. The precipitate was collected by filtration and washed with hexanes to afford the title compound of Step B (25.57 g) as a beige solid. 1 H NMR (CDCl3): delta 9.22 (br s,1H), 7.75 (d,1H), 7.40 (d,1H), 7.14 (t,1H), 5.32 (br s,1H), 3.88 (s,3H), 2.66 (s,6H), 2.35 (s,3H).

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; E. I. du Pont de Nemours and Company; US5962436; (1999); 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. 103-09-3, name is 2-Ethylhexyl acetate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H20O2

In the mechanical stirrer, reflux condenser and a thermometer of the 1000 ml flask of three sequentially added in the methyl acetate 296 g, isooctanol 260 g toluene sulfonic acid and 13.0 g, stir, for 65 C reaction 4 hours. By reducing pressure low boiling, then adding to the methoxy benzaldehyde 180 g, dropping 30% of 36 g liquid sodium methoxide. The reaction temperature is raised to 90 C, reaction 4 hours later. Gradually adding glacial acetic acid 7.9 g out-in and. By reducing pressure low boiling, filtering to remove the mother liquor solids, then the gas phase chromatography analysis, calculated in the mother liquor to the methoxy cinnamic acid ester product 376 g, yield 98.2%.

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; Shandong Daguan Biochemical Technology Co., Ltd.; Qingdao University of Science and Technology; Zhang Yongfu; Liu Baowei; Xu Zhihua; Jiang Yunbing; Yang Fengke; (6 pag.)CN107522616; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 185312-82-7, name is Methyl 4-bromo-2-chlorobenzoate, 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 185312-82-7, Computed Properties of C8H6BrClO2

Reference Example 12 4-bromo-2-chlorobenzyl alcohol Methyl 4-bromo-2-chlorobenzoate (477 g) of Reference Example 11 was dissolved in a mixed solution of ethanol (3000 mL) and water (680 mL), calcium chloride (212.2 g) was added at 10C, and the mixture was stirred for 30 min. To the solution was added sodium borohydride (144.7 g) by portions so that the inside temperature would not exceed 25C, and the mixture was stirred at room temperature for 5 hr. 1M Hydrochloric acid (5100 mL) was added dropwise to the reaction mixture, and the reaction solvent was evaporated under reduced pressure. Water and ethyl acetate were added to the residue. After partitioning and extraction, the organic layer was washed with 25% brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (399 g) as white crystals. 1H-NMR(CDCl3)delta(ppm):1.87(1H, t, J=5.8Hz), 4.74(2H, d, J=5.8Hz), 7.38(1H, d, J=8.2Hz), 7.42(1H, dd, J=1.8, 8.2Hz), 7.53(1H, d, J=1.8Hz).

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; Mitsubishi Tanabe Pharma Corporation; EP2017257; (2009); A1;,
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Related Products of 924-99-2, A common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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.

General procedure: Ethyl 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tertahydropyrimidine-5-carboxylate 6a (Table 2, entry 1). To a mixture of thiourea 12a (23.0 mg, 0.302 mmol), 4-chlorobenzaldehyde 13a (63.0 mg, 0.448 mmol), and ethyl 3-dimethylaminoacrylate 9 (64.0 mg, 0.447 mmol) in anhydrous DMF (0.3 mL) was added anhydrous aluminum chloride (8.0 mg, 0.0600 mmol) at room temperature, and the reaction mixture was stirred at 110 C for 3 h. To the mixture was added EtOAc (10 mL) and 1 M HCl aqueous solution (5 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (10 mL), and the combined organic layers were washed with water (5 mL) and brine (5 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane-EtOAc (4:1 to 2:1)] to give 6a (78.9 mg, 0.266 mmol, 88%) as pale yellow crystals.

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:
Article; Arai, Rie; Cho, Hidetsura; Gokurakuji, Yuki; Kikuchi, Hidetomo; Kubo, Takanori; Nakamura, Yuri; Nishimura, Yoshio; Sunaga, Katsuyoshi; Yuan, Bo; Tetrahedron Letters; (2020);,
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Synthetic Route of 25542-62-5, The chemical industry reduces the impact on the environment during synthesis 25542-62-5, name is Ethyl 6-bromohexanoate, I believe this compound will play a more active role in future production and life.

In a 50-mL round bottom flask, a stirred solution of substituted 5-bromo-2-hydroxybenzaldehyde (5.0 g, 24.8 mmol) in DMF (30 mL), was treated with potassium carbonate (10.26g, 74.4 mmol) and ethyl 6- bromohexanoate (6.6g, 29.8 mmol) at rt under nitrogen atmosphere. The reaction mixture was heated at 90C for 4 h. Upon completion of the reaction (TLC) the reaction mixture was cooled to rt, diluted with cold water and extracted ethyl acetate (250 mL x 2). The combined organic extract was washed with brine and dried over anhydrous NaiSO t. The solution was concentrated under reduced pressure to give the title compound (7.97 g, 94%) as yellow oil. LCMS (m/z): 343.2 (M+l)+.

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; SALK INSTITUTE FOR BIOLOGICAL STUDIES; MITOKYNE, INC.; EVANS, Ronald; BAIGA, Thomas, J.; BOCK, Mark, G.; DOWNES, Michael; EMBLER, Emi, Kanakubo; FAN, Weiwei; KEANA, John, F.W.; KLUGE, Arthur, F.; NOEL, Joseph, P.; PATANE, Mike, A.; WO2014/165827; (2014); 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 869-10-3 as follows. Computed Properties of C10H16Br2O4

A solution of diethyl 2,5-dibromoadipate (8.0 g, 0.0222 mol) in toluene (25 mL) was heated at 80C. After stopping the heating, 2-methoxyaniline (4.1 g, 0.333 mol) was added dropwise thereto over 40 minutes, and then the mixture was stirred for 11 hours at 100C again. The reaction mixture was filtrated by aspiration, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography to give 2.08 g of the title compound as a white solid. 1H-NMR (CDCl3) delta; 1.25 (6H, t, J=7.2Hz), 2.21 (4H, m), 3.71 (3H, s), 4.21 (4H, m), 4.36 (2H, m), 6.70 (1H, m), 6.82 (3H, m).

According to the analysis of related databases, 869-10-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1679069; (2006); A1;,
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Reference of 4224-69-5, 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. 4224-69-5, name is Methyl 2-(bromomethyl)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(2) To an anhydrous THF solution (2 ml) of the above-obtained Compound (8) (A=-CH=CH-CH=CH-, PG=TBS, 24(E)) (48 mg, 76.8 mumol) were added zinc (powder) (8 mg, 0.12 mmol), methyl 2-(bromomethyl)acrylate (13.8 mul, 0.12 mmol) and a saturated ammonium chloride aqueous solution (0.7 ml) at 0C, and the mixture was stirred for 30 min at room temperature. The reaction was quenched with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by column chromatography (5%?20% ethyl acetate in hexane) to obtain Compound (C) (60 mg, 107% yield). Compound (C):1H NMR (CDCl3) delta : 0.055 (s, 3 H), 0.059 (s, 3 H), 0.062 (s, 6 H), 0.55 (s, 3 H), 0.88 (s, 18 H), 1.04 (d, J=6.6 Hz, 3 H), 1.23-2.17 (m, 15 H), 2.18-2.24 (m, 1 H), 2.42-2.52 (m, 2 H), 2.60-2.65 (m, 1 H), 2.78-2.86 (m, 1 H), 3.74 (s, 3 H), 4.19-4.22 (m, 1 H), 4.28-4.34 (m, 1 H), 4.34-4.39 (m, 1 H), 4.86 (d, J=2.2 Hz, 1 H), 5.17 (s, 1 H), 5.53-5.62 (m, 1 H), 5.67 (d, J=1.2 Hz, 1 H), 5.90-6.03 (m, 2 H), 6.15-6.25 (m, 2 H), 6.26 (d, J=1.2 Hz, 1 H). MS m/z 747 (M+23)+.

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 2-(bromomethyl)acrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TEIJIN LIMITED; EP1477483; (2004); A1;,
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Application of 89-91-8,Some common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, molecular formula is C5H10O4, 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 solution of 2-chlorobenzylamine (30.0 g, 212 mmol) in MeOH (200 mL) was added triethylamine (36.7 mL, 265 mmol) and methyl dimethoxyacetate (31.0 g, 233 mmol). The reaction was heated to 80 C for 20 h. After cooling to room temperature, the reaction wasconcentrated in vacuo. EtOAc (300 ml) was added, washed with iN HC1 (300 mL x 2) and sat. aq. NaHCO3 (300 mL x 2). The organic layer was dried over anhydrous Na2SO4, filtered andconcentrated in vacuo to give the title compound (40.0 g, crude) as colorless oil that required no further purification. ?H NMR (400 IVIFIz, CDC13) 7.39 – 7.33 (m, 2H), 7.24 – 7.21 (m, 2H),4.73 (s, 1H), 4.56 (d, J 6.0 Hz, 2H), 3.38 (s, 6H).

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

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
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