Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 6091-64-1, name is Ethyl 2-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 6091-64-1, COA of Formula: C9H9BrO2

General procedure: In a 10 mL schlenk tube with magnetic stirring bar, cercosporin(0.05 equiv), aryl halide 1 (0.2 mmol), arene 2 (20 equiv), DIPEA (4equiv) were dissolved in CH3CN (2 mL) and the resulting mixtures were placed under 23WCFL under N2 atmosphere. When the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was reextracted with ethyl acetate. The combined organic extracts were dried over Na2SO4, concentrated in vacuum,and the resulting residue was purified by silica gel column chromatographyto afford the desired product 3.

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:
Article; Tang, Zhaocheng; Li, Jia; Lin, Fulin; Bao, Wenhao; Zhang, Shiwei; Guo, Baodang; Huang, Shuping; Zhang, Yan; Rao, Yijian; Journal of Catalysis; vol. 380; (2019); p. 1 – 8;,
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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. 2876-78-0, name is Methyl 1-Naphthaleneacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Methyl 1-Naphthaleneacetate

Triflic anhydride (16.6 mL, 0.099 mmol) was added dropwise to a solution of diphenylsulfoxide (10.0 g, 49.4 mmol) and methyl 2-(naphthalen-1-yl)acetate (10.9 g, 54.5 mmol) in DCM (100 mL) at -78 C. and stirred for 3 h. The reaction was quenched by the slow addition of water (50 mL) and slowly warmed to r.t. The layers were separated and the organic layer washed with 2M aqueous sodium iodide (10¡Á100 mL), and water (3¡Á100 mL), then concentrated to a viscous oil which was precipitated from MTBE (600 mL) to afford the title compound (18.7 g, 74%) as a light brown hydroscopic solid. 1H NMR (500 MHz, (CD3)2CO) delta: 8.48-8.51 (m, 1H), 8.30-8.33 (m, 1H), 8.03-8.10 (m, 3H), 7.75-7.99 (m, 8H), 7.72 (d, J=8 Hz, 1H), 4.39 (s, 2H), 3.68 (s, 3H).

The synthetic route of 2876-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Electronic Materials, LLC; LaBeaume, Paul J.; (24 pag.)US9304394; (2016); B2;,
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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. 185312-82-7, name is Methyl 4-bromo-2-chlorobenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 4-bromo-2-chlorobenzoate

Step A. 2-Chloro-4-(3-dimethylaminopropyl-1-yl)-benzoic acid methyl ester Under an atmosphere of nitrogen, a mixture of 4-bromo-2-chlorobenzoic acid methyl ester (25.13 g, 101 mmol), 1-dimethylamino-2-propyne (16 mL, 150 mmol), bis(triphenylphosphine)palladium(II) chloride (1.0 g) and copper (I) iodide (0.15 g) in 100 mL of triethylamine was heated at 60 C. for 2 hours. The cooled reaction mixture was filtered through Solka floc and the cake was washed with ethyl acetate. The filtrate was partitioned between ethyl acetate and dilute aqueous sodium thiosulfate. The organic layer was washed with water, brine and dried over sodium sulfate. The dark solution was filtered through a plug of Merck-60 silica gel and the filtrate was concentrated in vacuo to give the title compound (23.8 g, 95%) as an orange oil, which was used as such in the next step. NMR (DMSO-d6, 300 MHz): delta 2.25 (s, 6H, NCH3), 3.475 (s, 2H, CCH2N), 3.84 (s, 3H, OCH3), 7.5 (dd, 1H), 7.62 (s, 1H), 7.8 (d, 1H).

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; American Home Products Corporation; US6194407; (2001); B1;,
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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 206551-41-9 as follows. Application In Synthesis of Methyl 3-bromo-2-fluorobenzoate

Methyl 3-bromo-2-fluorobenzoate (500 mg, 2.15 mmol) dissolved in diethyl ether (15 mL) was cooled to 0 ¡ãC and treated with lithium aluminum hydride (81 mg, 2.13 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 6h. The reaction mixture was againcooled to 0 ¡ãC and methanol was added dropwise slowly followed by water. The reaction mixture wasdiluted with ethyl acetate and washed with water. The organic layer was concentrated to give (3-bromo- 2-fluorophenyl)methanol.

According to the analysis of related databases, 206551-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; APPLEBY, Todd; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; GUERRERO, Juan A.; JABRI, Salman Y.; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; NOTTE, Gregory; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (724 pag.)WO2018/195321; (2018); A1;,
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Synthetic Route of 3196-23-4, 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. 3196-23-4, name is Methyl 1-bromocyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

AD3 (R1 and R2 together formed a cyclohexyl ring) was mixed with BocNHOH in DMSO and treated with NaH (1 equiv.) at 50 0C overnight. After aqueous work up, the crude mixture was then treated with TFA to afford AD4 (R1 and R2 together formed a cyclohexyl ring) as the TFA salt.

The chemical industry reduces the impact on the environment during synthesis Methyl 1-bromocyclohexanecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; ZHU, Zhaoning; GREENLEE, William, J.; LI, Hongmei; VICAREL, Monica, L.; QIN, Jun; DHONDI, Pawan, Kumar; HUANG, Xianhai; PALANI, Anandan; LIU, Xiaoxiang; SUN, Zhong-Yue; JOSIEN, Hubert B.; XU, Ruo; COLE, David, James; BURNETT, Duane, A.; BENNETT, Chad, E.; MCCRACKEN, Troy, M.; MACCOSS, Malcolm; WO2010/56722; (2010); A1;,
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Electric Literature of 91-44-1, 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. 91-44-1 name is 7-(Diethylamino)-4-methyl-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.

General procedure: In a Schlenk tube, coumarin 1 (0.5mmol), dialkyl H-phosphite 2 (1.0mmol), AgNO3 (0.025mmol, 4.2mg) and Mg(NO3)2¡¤6H2O (0.25mmol, 64mg) were added and charged with Nitrogen (3 cycles). Anhydrous CH3CN (1mL) was then added. After heating in the oil bath at 100C for 6h (monitored by TLC), 5mL ethylacetate was added to dilute the reaction solution. The solution was filtrated, and the solvent was distilled under vacuum. The crude product was purified by silica gel column chromatography to give the desired product 3 using ethylacetate/petroleum ether (1:5 to 2:1) as eluant.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-(Diethylamino)-4-methyl-2H-chromen-2-one, and friends who are interested can also refer to it.

Reference:
Article; Yuan, Jin-Wei; Li, Yuan-Zhe; Yang, Liang-Ru; Mai, Wen-Peng; Mao, Pu; Xiao, Yong-Mei; Qu, Ling-Bo; Tetrahedron; vol. 71; 42; (2015); p. 8178 – 8186;,
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Electric Literature of 2967-66-0,Some common heterocyclic compound, 2967-66-0, name is Methyl 4-(trifluoromethyl)benzoate, molecular formula is C9H7F3O2, 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.

Step 2: To a solution of anhydrous hydrazine in anhydrous toluene is added methyl 4-(trifluoromethyl) benzoate (4). The reaction solution is heated at reflux for 18 hours under a nitrogen atmosphere. After cooling to 40-50C, the solvent is evaporated under reduced pressure. The resulting solid is recrystallized from tert-butyl methyl ether to give hydrazide (5) as a white solid.

The synthetic route of 2967-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Siga Technologies, Inc.; JORDAN, Robert; BAILEY, Thomas, R.; RIPPIN, Susan R.; DAI, Dongcheng; (69 pag.)EP3006425; (2016); A1;,
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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. 3469-00-9, name is Methyl Diphenylacetate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Step 1 : Methyl 2.2-bis(4-nitrophenyl)acetate (8). Compound 7 (6 g, 26.5 mmol) was dissolved in fuming nitric acid (60 mL) and stirred at room temperature for 16 h. The reaction mixture was poured onto ice, the resulting light yellow sludge was separated out then dissolved in ether to provide a solid. Filtration afforded title compound 8 as a white solid (1.15 g, 14%). 1H NMR (DMSO-d6) delta (ppm):8.22 (d, J = 9.0 Hz, 4H), 7.65 (d, J = 8.6 Hz, 4H), 5.76 (s, IH), 3.72 (s, 3H).

The synthetic route of 3469-00-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METHYLGENE INC.; WO2008/122115; (2008); 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. 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H13BrO2

A mixture of 4-hydroxy-2-methylindole (1) (1.5 g, 0.010 mole), 2-bromo-3-methyl-butyric acid ethyl ester (2.2 g, 0.010 mole) and potassium carbonate (excess) in acetone (50 mL) was refluxed for 3 days. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by column chromatography (20:1 Hex:EtOAc) to afford intermediate 2. Yield: 1.88 g, 71%

According to the analysis of related databases, 609-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); A1;,
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Electric Literature of 28170-07-2, 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. 28170-07-2, name is Benzyl phenyl carbonate, This compound has unique chemical properties. The synthetic route is as follows.

According to: Pittelkow, M.; Lewinsky, R.; and Christensen, J. B. Synthesis 2002, 15, 2195-2202.Benzyl phenylcarbonate (25,1 g, 1 10 mmol) was added dropwise to a solution of diethylenetriamine (5,16 g, 50 mmol) in dichloromethane (100 ml). The mixture was stirred for at least 20 h. The organic phase was washed with phosphate buffer (0.025 M K2HPO4,0.025 M NaH2PO4, 2000 ml, pH adjusted to 3 with 2 M sulfuric acid). The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo.Yield: 25.2 g A portion (5 g) of the crude oil was mixed with hydrochloric acid (2 M, 15 ml). The mixture was stirred for 15 minutes. The mixture was filtered. The isolated solid was mixed with abs. ethanol (600 ml). The mixture was brought to reflux. The boiling mixture was decanted in order to remove insoluble impurities. The compound crystallized over night at 5 C.Yield: 2.84 g (white crystals) 1H-NMR (af-DMSO) delta: 8.96 (b, 2H), 7.51 (t, J = 5.56 Hz, 2H), 7.40-7.30 (b, 10H), 5,04 (s,4H), 3.33 (q, J = 6.06 Hz, 4H), 3.00 (b, 4H)13C- NMR (Gf-DMSO) delta: 156.6, 137.2, 128.7, 128.3, 128.2, 66.0, 46.8, 37.1LC-MS (ES-positive mode), m/z: 372.5 [M+H]+

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

Reference:
Patent; NOVO NORDISK A/S; WO2006/87354; (2006); A2;,
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