Category: 2905-65-9

Synthetic Route of 2905-65-9,Some common heterocyclic compound, 2905-65-9, name is Methyl 3-chlorobenzoate, molecular formula is C8H7ClO2, 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: The following experimental procedure for the partial reduction of ethyl benzoate to benzaldehyde is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with ethyl benzoate (0.07 mL, 0.5 mmol) and THF (5 mL). After cooling to 0 C, cis-2,6-dimethylmorpholine-modified Red-Al (2.5 mL, 0.4 M 1.0 mmol) was added dropwise and the mixture was stirred for 30 min at the room temperature. The reaction was stopped aqueous 1 N HCl (5 mL) and the product was extracted with diethyl ether (10 mL). The ether layer was dried over anhydrous magnesium sulfate. GC analysis showed a 98% yield of benzaldehyde. All products in Table 1 were confirmed through comparison with GC data of authentic sample.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-chlorobenzoate, its application will become more common.

Reference:
Article; Shin, Won Kyu; Kang, Daehoon; An, Duk Keun; Bulletin of the Korean Chemical Society; vol. 35; 7; (2014); p. 2169 – 2171;,
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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. 2905-65-9, name is Methyl 3-chlorobenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-chlorobenzoate

Pd(OAc)2 or Pd2(dba)3/2-Catalyzed Amination of Aryl chlorides (Table 5).General Procedure: An oven-dried Schlenk flask equipped with a magnetic stirring bar was charged with Pd(OAc)2 or Pd2(dba)3 (x mol %, see Table 5) and NaO-t-Bu (1.5 mmol) or Cs2CO3 (1.5 mmol). Amine (1.2 mmol) and aryl chloride (1.0 mmol) were also added at this time if they were solids. The flask was capped with a rubber septum, evacuated and then flushed with argon. This cycle was repeated three times. Ligand 2 (2x mol %, see Table 5) was then added via syringe from a stock solution. Aryl chloride (if a liquid, 1.0 mmol), amine (if a liquid, 1.2 mmol) and toluene (3 mL) were then successively added by syringe. The reaction mixture was heated at 110 C. until the starting material had been completely consumed as judged by TLC (24 hours). The mixture was cooled to room temperature, adsorbed onto silica gel and then purified by column chromatography (hexanes/ethyl acetate as eluent).

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; Iowa State University Research Foundation, Inc.; US7385058; (2008); B1;,
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Ester – an overview | ScienceDirect Topics

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. 2905-65-9, name is Methyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2905-65-9

General procedure: To a solution of methyl ester of aromatic carboxylic acid 2 (0.1 mol) in methanol (30 mL), hydrazine hydrate (0.2 mol) was added drop wise with stirring. The resulting mixture was allowed to reflux for 8 h. After the completion of the reaction as monitored by TLC, the excess methanol was distilled off under reduced pressure. The resulting acid hydrazide 3 was washed with cold water, dried and recrystallized from ethanol.

The synthetic route of 2905-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Murty, Madugula S.R.; Katiki, Mohana R.; Rao, Busam R.; Narayanan, Sai S.; Anto, Ruby J.; Buddana, Sudhreer K.; Prakasham, Reddy S.; Devi, Bethala L.A.P.; Prasad, Rachapudi B.N.; Letters in drug design and discovery; vol. 13; 9; (2016); p. 968 – 981;,
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Reference of 2905-65-9, 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. 2905-65-9, name is Methyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

NaHMDS (2M, 5.50 mL) was added to a solution of pent-4-enenitrile (0.97 mL, 10.0 mmol) in anhydrous THF (50 mL) at -78 oC. After stirring for 15 min, methyl-3-chlorobenzoate (1.88 g) was added and the reaction was stirred for 30 min befor warming to room temperature. The reaction was quenched by addition of 1N HCl solution, then extracted with EtOAc (x 2). The combined organics were dried and concentrated to give the acylated nitrile (2.18 g, 99%). Hydroxylamine hydrochloride (382 mg) was added to a solution of the acylated nitrile (1.1 g) in pyridine (10 mL) and the reaction was stirred at 80 oC for 3 hours. After cooling to room temperature, EtOAc and sat. NH4Cl solution were added and the layers separated. The organic was washed with brine, dried over Na2SO4 and concentrated to give the amino-isoxazole as a yellow oil (1.05 g, 89%) which was used directly. The residue was dissolved in pyridine (5 mL) and cooled in an ice-bath. AcCl (0.36 g, 4.5 mmol) was added and the reaction was stirred for 30 min before warming to room temperature for a further 30 min. The volatiles were removed under vacuum and the residue was purified by silica gel chromatography [heptane/EtOAc, 9:1 – 3:1] to give the product as a colourless oil (0.96 g, 77%). The N-acyl intermediate (950 mg, 3.43 mmol) was then N-alkylated with allyl bromide and NaH to give the product 19 as a colourless oil (855 mg, 79%)

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

Reference:
Article; Moss, Thomas A.; Tetrahedron Letters; vol. 54; 8; (2013); p. 993 – 997;,
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Ester – an overview | ScienceDirect Topics

Application of 2905-65-9, 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. 2905-65-9, name is Methyl 3-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Pd(OAc)2 or Pd2(dba)3/2-Catalyzed Amination of Aryl chlorides (Table 5).General Procedure: An oven-dried Schlenk flask equipped with a magnetic stirring bar was charged with Pd(OAc)2 or Pd2(dba)3 (x mol %, see Table 5) and NaO-t-Bu (1.5 mmol) or Cs2CO3 (1.5 mmol). Amine (1.2 mmol) and aryl chloride (1.0 mmol) were also added at this time if they were solids. The flask was capped with a rubber septum, evacuated and then flushed with argon. This cycle was repeated three times. Ligand 2 (2x mol %, see Table 5) was then added via syringe from a stock solution. Aryl chloride (if a liquid, 1.0 mmol), amine (if a liquid, 1.2 mmol) and toluene (3 mL) were then successively added by syringe. The reaction mixture was heated at 110 C. until the starting material had been completely consumed as judged by TLC (24 hours). The mixture was cooled to room temperature, adsorbed onto silica gel and then purified by column chromatography (hexanes/ethyl acetate as eluent).

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

Reference:
Patent; Iowa State University Research Foundation, Inc.; US7385058; (2008); B1;,
Ester – Wikipedia,
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. 2905-65-9, name is Methyl 3-chlorobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H7ClO2

General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ¡À 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ¡À 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized. The synthetic route of 2905-65-9 has been constantly updated, and we look forward to future research findings. Reference:
Article; Malineni, Jagadeesh; Jezorek, Ryan L.; Zhang, Na; Percec, Virgil; Synthesis; vol. 48; 17; (2016); p. 2795 – 2807;,
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Electric Literature of 2905-65-9, 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. 2905-65-9, name is Methyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Substituted benzoic acid (1.0 mmol) was dissolved in thionylchloride and refluxed for 2 h, then the solvent was removed underreduced pressure to obtain the white solid. The white solid in methanol was added concentrated sulfuric acid (1 mL) and themixture was refluxed for 4 h, the solvent was removed to obtaincrude solid. The crude solid was extracted with ethyl acetate andwater. The solvents were evaporated to afford the pure product.Finally, the pure product was dissolved in ethanol, and the hydrazinehydrate was added. The mixture was refluxed for 9 h, and thesolvent was removed

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

Reference:
Article; Lian, Zhi-Min; Sun, Juan; Zhu, Hai-Liang; Journal of Molecular Structure; vol. 1117; (2016); p. 8 – 16;,
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Related Products of 2905-65-9, 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 2905-65-9 as follows.

This example illustrates the tandem Ir-catalyzed borylation and catalytic amination process. [0064] 3-Aminoboronic acids and esters as shown below are of interest as evidenced by the large number of derivatives synthesized, and by several patents, which note their activity as O-lactamase inhibitors (See, for example, Shoichet et al., WO0035905). Few in number, however, are 1, 3, 5-aminoboronic acids and esters (about 25 compounds by SCIFINDER SCHOLAR). Such substrates may prove useful for further derivatization as they can possess three unique sites for diversity. Furthermore, these compounds may prove ideal as scaffolds for combinatorial libraries. The boronic acid or ester can be transformed into a myriad of functionalities including aryl or vinyl via the Suzuki-Miyuara coupling (Miyaura and Suzuki, Chem. Rev. 95: 2457-2483 (1995); Suzuki, J. Organomet. Chem. 576: 147-168 (1999); Miyaura, In Advances in Metal-Organic Chemistry: Liebeskind, Ed.: JAI: London,; Vol. 6, pp. 187-243 (1998)). If R is a halogen, then there exists a multitude of coupling opportunities (See, for examples, Metal-catalyzed Cross-coupling Reactions; Diederich and Stang, eds.: Wiley: Wienheim, 1998). [0066] Recently, a catalytic aromatic C-H activation/borylation reaction utilizing Ir- or Rh-catalysts was developed. The process is high yielding, functional group tolerant (alkyl, halo, carboxy, alkoxy, and protected amino), chemoselective (1,3-substited arenes give only the 5-boryl product), and efficient (Iverson and Smith, J. Am. Chem. Soc. 121: 7696-7697 (1999); Cho et al., J. Am. Chem. Soc. 122: 12868-12869 (2000); Tse et al., Org. Lett. 3: 2831 (2001); Chao et al., Science 295: 305-308 (2002)). Furthermore, the process allows for the direct construction of aryl boronic esters from hydrocarbon feedstocks without going through an aryl halide. Scheme 2 depicts a prototypical borylation reaction: borylation of benzene using (Ind)Ir(COD)(2 mol %), dppe (2 mol %). The borane of choice is pinacolborane (HBPin). A variety of Ir(I) catalysts can be used, including [Ir(COD)Cl]2, Ir(Indenyl)(C2H4)2, Ir(Indenyl)dppe, and (Indenyl)Ir(COD), in the presence of 2 mol equivalents of PMe3 or 1 mol equivalent of a bidentate ligand like dmpe or dppe. The catalyst system of choice is (Indenyl)Ir(COD), dppe or dmpe (2 mol % each) because of it’s cleanness of reaction and efficient TOF (24 h-1 with benzene). The reaction can be run in the neat arene or in inert solvents (e.g. cyclohexane). During our studies into tandem borylation/Suzuki coupling, we noted difficulties with the hydrolysis of the boronic ester functionality (Bpin). The robustness of the BPin group suggested that, perhaps, the pinacol might serve as a protecting group for the boron. Thus, it was deemed of interest to explore other catalytic transformations in the presence of the BPin group. One such transformation is the Buchwald-Hartwig amination of aryl halides (See, for example; Wolfe et al.,. J. Org. Chem. 65: 1158 (2000); Hartwig et al., J. Org. Chem. 64: 5575 (1999); Wolfe and Buchwald, Angew. Chem. Int. Ed. 38: 2413 (1999)). Initially, the reaction was attempted on pure 1-chloro-3-methylphenyl-5-BPin. As shown in Scheme 3 (Buchwald-Hartwig coupling of 1-chloro-3-methylphenyl-5-BPin with aniline), application of Buchwalds protocol proceeded cleanly to give the desired cross-coupling product in 64.7% and 63.8% yield. The use of PtBu3 improved the yield to 78.8%. Unfortunately, initial attempts to perform the reaction in the ?one-pot? protocol were unsuccessful. Table 1 summarizes the results. In all cases where K3PO4.nH2O was used, a significant amount of pinacol was observed by GC-FID (Entries 1-5). While this is indicative of reaction of the BPin group and is most likely a by-product of Suzuki coupling (in this case, dimerization or oligiomerization of the starting material), no dimers or oligiomers were isolated. Noteworthy, is the formation of the desired product, albeit in low yield (10% GC-FID ratio), using K3PO4.nH2O and PtBu3 when all other attempts using the base failed. With anhydrous K3PO4, results were better (Entries 6-9). Most importantly, no pinacol was formed in these reactions. Changing the base or increasing catalyst loading did not improve the results. The use of PtBu3 led to the best results and after 4 days at 100 C., 34.4% of the desired product was isolated (Entry 10). This result, however, falls short of the reaction performed on pure material and shows that the by-products from the Ir-catalyzed borylation are not completely innocuous. As was previously mentioned, a potential source of concern is the presence of free bidentate phosphines after the borylation, which may interfere with subsequent reactions. In the tandem Suzuki reactions, an aryl chloride was successfully coupled only when dmpe was used as the Ir ligand. Thus, the tandem borylation/Buchwald-Hartwig amination reaction of the present invention was attempted using the (Ind)Ir(COD)/dmpe precatalyst….

According to the analysis of related databases, 2905-65-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Board of Trustees of Michigan State University; US2004/24237; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

2905-65-9, Adding some certain compound to certain chemical reactions, such as: 2905-65-9, name is Methyl 3-chlorobenzoate, 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 2905-65-9.

General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ¡À 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ¡À 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized. 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 2905-65-9. Reference:
Article; Malineni, Jagadeesh; Jezorek, Ryan L.; Zhang, Na; Percec, Virgil; Synthesis; vol. 48; 17; (2016); p. 2795 – 2807;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics