Month: August 2021

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. 4891-38-7, name is Methyl Phenylpropiolate, A new synthetic method of this compound is introduced below., COA of Formula: C10H8O2

General procedure: Steroidal/nonsteroidal bromo vinyl aldehyde (0.5 mmol), alkyne (0.5 mmol), benzyl amine (0.5 mmol), Pd(OAc)2 (5 mol%), PPh3 (10 mol%), Na2CO3 (1.5 mmol) and neutral alumina (200 mg) were mixed intimately and the mixture was irradiated in a closed vessel in a Synthos 3000 microwave reactor at 600 Watt (140 C and 12 bar) for 10 min. After 10 min ethylacetate (30 mL) was added to the reaction mixture and it was filtered through whatman filter paper. The residue obtained after removal of ethylacetate layer was purified by silica gel column chromatography using EtOAc/hexane as the eluent to afford the pyridine derivative. The alumina on the filter paper was then dried in vacuo and can be used again for another two times in place of Pd(OAc)2 without substantial loss of the yield of the product.

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; Shekarrao, Kommuri; Nath, Dipankar; Kaishap, Partha Pratim; Gogoi, Sanjib; Boruah, Romesh C.; Steroids; vol. 78; 11; (2013); p. 1126 – 1133;,
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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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C9H11NO2

General procedure: Water (4 mL) and HBF4 (~48-50% aq. sol., 4 mL) was added to the aniline (0.50 mmol, 1.0 equiv.) and stirred for a couple of minutes at room temperature in an open reaction flask. NaNO2 (0.038 g,1.1 equiv.) in water (2.8 mL) was added dropwise at 0C and stirred for 30 minutes. To the cold solution of the resulting diazonium salt was added sat. aq. copper(II)sulfate (50 mL), followed by copper(I)oxide (1.0 equiv., 0.072 g), and stirred at room temperature for 30 minutes. The reaction mixture was extracted with CH2Cl2, dried (MgSO4)and evaporated in vacuo. The crude products were purified by silica gel chromatography.Potential hazard note: Diazonium compounds can be explosive, however, the risk is greatly reduced by following several rules for precaution.[17]Additional points that render the experimental procedure reported herein safer is that the diazonium salt is prepared in situ under dilute conditions and is not isolated, the reaction is performed open to air, the reaction temperature is 0C to ambient, HBF4-is used as the counterion in this procedure, and arene diazonium tetra-fluoroborates, in contrast to the chloride salts, are renowned in general for their enhanced thermal stability and shockin sensitivity. Nevertheless, care should always be taken when handling diazonium compounds.

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; Kristianslund, Renate; Vik, Anders; Hansen, Trond V.; Synthetic Communications; vol. 48; 21; (2018); p. 2809 – 2814;,
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Synthetic Route of 455-68-5, The chemical industry reduces the impact on the environment during synthesis 455-68-5, name is Methyl 3-fluorobenzoate, I believe this compound will play a more active role in future production and life.

EXAMPLE 2 72.4 parts of methyl 3-fluorobenzoate are dissolved in 300 parts of 100percent strength sulfuric acid with stirring at not more than 30° C., the solution is cooled to 0°-10° C. and then, over the course of 2 hours, a mixture of 32.7 parts of 98percent strength nitric acid and 78.3 parts of 100percent strength sulfuric acid is added dropwise with continuous cooling at 0°-10° C., and the mixture is stirred without cooling for 3 hours, during which the temperature of the nitrating mixture rises to 20° C. Then 175 parts of water are added dropwise, again with continuous cooling. The methyl fluoronitrobenzoate separates out as an oil which is separated off, washed until neutral in portions with 350 parts of water, and dried in vacuo at 100° C. 92 parts of methyl fluoronitrobenzoate are obtained, comprising 98.1percent methyl 5-fluoro-2-nitrobenzoate and 1.9percent methyl 3-fluoro-2-nitrobenzoate, with an s.p. of 34.0° C. and a purity (GC) of >99percent based on isomer mixture.

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

Reference:
Patent; Hoechst Aktiengesellschaft; US5543550; (1996); A;,
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Application of 31930-34-4, 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. 31930-34-4 name is Ethyl cis-3-Bromoacrylate, 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 dry and argon-flushed 10 mL Schlenk-tube, equipped with a stirring bar and a septum, was charged with dryCoCl2 (6.5 mg, 0.05 mmol, 5 mol%) and dry THF (2.0 mL). The respective aryl halide (1.0 mmol, 1.0 equiv) wasadded at room temperature. Then, a solution of the appropriate (hetero)aryl zinc pivalate (1.5 mmol, 1.5 equiv)was added dropwise over 5 min via syringe. The reaction was stirred at 40 C and monitored by GC-analysis(C11H24 was used as an internal standard). Upon consumption of the starting material, saturated aqueous NH4Clsolution (5 mL) and ethyl acetate (5 mL) were added, the phases were separated and the aqueous phase was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with aqueous NaOHsolution (2 M, 50 mL) and dried over Na2SO4. The solvents were evaporated and the residue was subjected tocolumn chromatography purification on silica yielding the respective title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl cis-3-Bromoacrylate, and friends who are interested can also refer to it.

Reference:
Article; Hofmayer, Maximilian S.; Hammann, Jeffrey M.; Lutter, Ferdinand H.; Knochel, Paul; Synthesis; vol. 49; 17; (2017); p. 3925 – 3930;,
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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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 3-bromo-4-fluorobenzoate

Sodium hydride (0.88 g, 22 mmol, 60% w/w) was added to N,N (1r,4r)-4-methylcyclohexane-1-ol (0.84 g, 7.3 mmol) at 0 C – in dimethylformamide (30 mL) solution. The reaction solution was stirred at 0 C for 10 minutes. Then, methyl 3-bromo-4-fluorobenzoate (1.8 g, 8.2 mmol) was added, and the mixture was stirred at room temperature for 10 hours. The reaction was quenched with saturated ammonium chloride, ethyl acetate (50mL * 2), washed with saturated brine (20mL * 5) The organic phase was dried and evaporated to dryness to give a crude product. The crude product was subjected to column separation (petroleum ether: ethyl acetate = 20:1) to give a methyl group. 3-Bromo-4-(((1r,4r)-4-methylcyclohexyl)oxo)benzoate (1.2 g, yield 50%).

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 82702-31-6.

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Ye Guozhong; Liu Lei; Bao Rudi; Wu Shenghua; Deng Haining; (130 pag.)CN110041253; (2019); A;,
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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. 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate

Preparation of intermediate 5B:l-(((5-bromopyrimidin-2-yl)oxy)methyl)cyclopropane carboxylic acid ethyl ester5-Bromo-2-hydroxypyrimidine (850 mg, 4.86 mmol) and triphenylphosphine (1.91 g, 7.3 mmol) were dissolved in THF, to which was added diisopropyl azodicarboxylate DIAL) (1.19 mL, 6 mmol). The reaction solution was stirred at room temperature for 1 h, after which was added l-(hydroxymethyl)cyclopropanecarboxylic acid ethyl ester 5A (700 mg, 4.86 mmol). The reaction proceeded overnight at room temperature under stirring. The solvents were evaporated and the residue was purified with a silica gel column (n-hexane: ethyl acetate = 20: 1) to give 580 mg of white solid 5B. Yield: 39.7%.MS (ESI, m/z): [M+H]+: 300.9; 1H-NMR (300 MHz, CDC13): 8.55 (s, 2H), 4.53 (s, 2H), 4.16 (q, 2H, J= 7.2 Hz), 1.41(dd, 2H, J = 4.2 Hz, J = 3.0 Hz), 1.23 (t, 3H, J= 7.2 Hz), 1.06 (dd, 2H, J = 4.2 Hz, J= 3.0 Hz).

According to the analysis of related databases, 3697-68-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIJING HANMI PHARMACEUTICAL CO., LTD; ZHANG, Bo; YANG, Jun; LIU, Jinming; HUANG, Hai; WU, Yong; TAO, Ran; XU, Jiangcheng; SHEN, Ning; MOON, Sunghwan; KIM, Maengsup; WO2013/56679; (2013); 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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 4-bromo-3-fluorobenzoate

a- Synthesis of Int. 272: In a microwave vial, a mixture of methyl 4-bromo-3-fluorobenzoate (1.00 g 4.3 mmol), cyclopropylboronic acid (1.1 g, 13 mmol) and KF (0.75 g, 13 mmol) in dry toluene (10 mL) was purged with N2. Pd(PPh3)4 (0.25 g, 0.22 mmol) was added and the mixture was purged again with N2 and heated at 150C for 2h. The crude was partitioned between DCM and water. The organic layer was separated, dried over MgS04, filtered through a pad of silica gel and evaporated in vacuo to give 0.85 g of Int. 272 (quant.) which was used as such in the next reaction step.

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MEVELLEC, Laurence, Anne; PASQUIER, Elisabeth, Therese, Jeanne; DESCAMPS, Sophie; MERCEY, Guillaume, Jean, Maurice; WROBLOWSKI, Berthold; VIALARD, Jorge, Eduardo; MEERPOEL, Lieven; JEANTY, Matthieu, Ludovic; JOUSSEAUME, Thierry, Francois, Alain, Jean; WO2015/144799; (2015); A1;,
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Related Products of 4891-38-7, 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 4891-38-7 as follows.

General procedure: A 25 mL Schlenk tube equipped with a magnetic stirringbar was charged with I2 (12.7 mg, 0.05 mmol), substituted thiol1 (0.5 mmol) and alkyne 2 (0.75 mmol). The tube was evacuatedtwice and backfilled with nitrogen, and DTBP (2.5 mmol)was added into the tube under nitrogen atmosphere. The tubewas sealed with a balloon and the mixture was stirred undernitrogen atmosphere at 110 C for 18 h. Upon completion of thereaction, the resulting solution was cooled to r.t., and thesolvent was removed with the aid of a rotary evaporator. Theresidue was purified by column chromatography on silica gel(PE-EtOAc) to give 3.

According to the analysis of related databases, 4891-38-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yan, Kelu; Yang, Daoshan; Zhang, Mengqi; Wei, Wei; Liu, Yao; Tian, Laijin; Wang, Hua; Synlett; vol. 26; 13; (2015); p. 1890 – 1894;,
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Application of 609-12-1, 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.

[00485] 2-(1’Benzyl’2-methyl-1H-indol-4’yloxy)-3-methyl-butyric acid ethyl ester 7:1-Benzyl-2-methyl-1H-indol-4-ol 3 (0.3 g 1.26 mmole) was dissolved in anhydrous dimethylformamide (20 ml_). To the solution sodium hydride 60% in mineral oil (66 mg 1.65 mmole) was added. The mixture was stirred at room temperature for 1 h. To the mixture ethyl-2-bromoisovalerate (0.344 mL, 1.65 mmole) was added. The mixture was stirred at room temperature for 18 h. The reaction was diluted with ethyl acetate (300 mL) and washed with H2O (4 x 100 mL) and brine (1 x 100 mL). The organic layer was separated, dried with magnesium sulfate and concentrated. The residue was purified by column chromatography (10:1 Hexane:EtOAc) to afford a 1 :1 mixture of 7:ethyl-2-bromoisovalerate. Further purification by column chromatography (10:1 Hexane.epsilontOAc) afforded 7 (0.09 g, 19 %) as a yellow oil.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-bromo-3-methylbutanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ILYPSA, INC.; WO2007/56279; (2007); A2;,
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These common heterocyclic compound, 55954-25-1, name is Methyl 2-(2,4-Dimethoxyphenyl)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. Product Details of 55954-25-1

This compound was prepared from compound 8 in three steps without purifying the intermediate acid and acid chloride. n-BuLi (2.5 M in THF, 0.87 mL, 2.18 mmol) was added drop wise to a stirred solution of 8 (420 mg, 1.82 mmol) in THF (10 mL) at -78 C under N2 atmosphere. After 30 min CO2 gas was passed through the solution during 45 min of time and the mixture was allowed to warm up to room temperature. THF was removed in vacuum and the mixture was treated with saturated NaHCO3 solution (30 mL). The water layer was washed with ethyl acetate (2*15 mL) and then acidified with conc. HCl. The mixture was extracted with ethyl acetate (2*50 mL). The organic layer was washed with water (2*20 mL), brine (20 mL), dried (Na2SO4), filtered and concentrated to get the acid 10 (320 mg). Without further purification it was dissolved in CH2Cl2 (10 mL) under N2 atmosphere, DMF (one drop) and oxalyl chloride (0.23 mL, 2.6 mmol) were added. The mixture was stirred for 3 h at room temperature and then the solvent was removed in vacuum to yield the corresponding acid chloride, which was again directly used for the next reaction without further purification. A solution of compound 1114 (514 mg, 2.45 mmol) in THF (7 mL) was added at -78 C to a freshly prepared solution of LDA, prepared from n-BuLi (2.5 M in THF, 1.3 mL, 3.26 mmol) and i-Pr2NH (0.45 mL, 3.26 mmol) in THF (5 mL) at 0 C under N2 atmosphere. The thus produced yellowish anion was stirred at -78 C for 45 min and then a solution of crude acid chloride, prepared earlier, in THF (10 mL) was added drop wise. The reaction was stirred at the same temperature for another 45 min and then at room temperature for 4 h. 10% HCl (10 mL) was added to quench the reaction, THF was removed in vacuum and the water layer was extracted with ethyl acetate (2*50 mL). The organic layer was washed with water (2*20 mL), brine (20 mL), dried (Na2SO4) and concentrated. The crude product was purified by silica gel column chromatography to get 13 (480 mg, 68% in three steps) as yellowish oily compound. Rf 0.5 (1:1 ethyl acetate:hexane); numax (CHCl3) cm-1 1732, 1659, 1608, 1508, 1463, 1211, 1029; 1H NMR (CDCl3, 500MHz): delta 7.71 (s, 1H, C6?-H), 7.01 (d, 1H, J=8.5Hz, C6?-H), 6.43 (s, 1H, C3?-H), 6.41 (d, 1H, J=8.5Hz, C5?-H), 6.28 (s, 1H, C3?-H), 5.94 (s, 1H, C2-H), 3.82 (s, 3H, OCH3), 3.76 (s, 3H, OCH3), 3.75 (s, 3H, OCH3), 3.74 (s, 3H, OCH3), 3.71 (s, 3H, CO2CH3), 2.10 (s, 3H, CH3); 13C NMR (CDCl3, 125MHz): delta 193.1 (C), 171.1 (C), 163.0 (C), 160.3 (C), 159.6 (C), 157.9 (C), 133.1 (CH), 130.1 (CH), 118.9 (C), 118.0 (C), 115.8 (C), 104.1 (CH), 98.4 (CH), 94.1 (CH), 57.2 (CH3), 55.5 (CH3), 55.3 (CH3), 55.2 (CH3), 55.2 (CH3), 52.1 (CH), 15.3 (CH3); HRMS (EI+) m/z 388.1529 ([M]+ C21H24O7, requires 388.1521).

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

Reference:
Article; Pahari, Pallab; Saikia, Ujwal Pratim; Das, Trinath Prasad; Damodaran, Chendil; Rohr, Juergen; Tetrahedron; vol. 72; 23; (2016); p. 3324 – 3334;,
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