Month: May 2021

Application of 331779-03-4, These common heterocyclic compound, 331779-03-4, name is Ethyl 2-(4-bromophenyl)acrylate, 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: To a solution of ester (20 mmol, 1.0 equiv) in toluene (40 mL) was addedparaformaldehyde (1.80 g, 60 mmol, 3.0 equiv), K2CO3 (8.29 g, 60 mmol, 3.0 equiv),n-Bu4NI (370.0 mg, 1.0 mmol, 0.05 equiv). The reaction mixture was heated to 60 Covernight. After the finish of reaction monitored by TLC, the reaction was cooled toroom temperature, water was added and the aqueous layer was extracted with Et2O(40 mL × 3). The combined organic layer was dried over anhydrous Na2SO4,concentrated in vacuo. The resulting residue was purified by column chromatographyto give the corresponding acrylate intermediate as a colorless oil. Then, a solution ofsubstituted amine (20 mmol, 2.0 equiv)in THF (13.0 mL) at 0C was added a solutionof corresponding acrylate (10 mmol, 1.0 equiv) in THF (7.0 mL) via addition funnel.The reaction mixture was allowed to warm to ambient temperature then stirred atroom temperature for 24h, and concentrated under vacuum. The resulting residue waspurified by column chromatography to give the corresponding intermediate as a oil.Then to a solution of the oil in dichloromethane (20.0 mL) were added di-tert-butyldicarbonate (2.40 g, 11 mmol) and DMAP (122.0 mg, 1 mmol), and the mixture wasstirred at room temperature for 24h. Saturated aq. NH4Cl was added to the mixtureand the resulting mixture was extracted with dichloromethane. The combined organiclayer was washed with brine, dried over Na2SO4, filtered and evaporated in vacuo.The resulting residue was purified by column chromatography to give thecorresponding intermediate as a colorless oil. Then to a solution of the resulting oil inTHF/H2O (5 mL/5 mL) was added LiOH (1.20 g, 50 mmol, 5 equiv). The reactionmixture was heated at 60 C overnight. After cooling to room temperature, thereaction was acidified using aqueous HCl (6 M), and the aqueous layer was extractedwith Et2O (20 mL × 3). The combined organic layer was washed with water and brine,dried over Na2SO4, and concentrated in vacuo to give the resulting product 4a-j as acolorless crystal, using for the next step without further purification.

The synthetic route of 331779-03-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Li; He, Gu; Pan, Zhaoping; Wu, Fengbo; Yu, Meng; Zeng, Minghui; European Journal of Medicinal Chemistry; vol. 189; (2020);,
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Related Products of 1462-12-0, A common heterocyclic compound, 1462-12-0, name is Diethyl 2-ethylidenemalonate, molecular formula is C9H14O4, 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: Isatin Schiff base 2 (22.2 mg, 0.1 mmol), the corresponding electrophile (0.2 mmol), and catalyst I (6.0 mg, 0.01 mmol) were stirred in toluene or 1,2-DCE (0.3 mL) at the reported temperature for the appropriate time (Tables 2 and 3). In the case of the reactions carried out at 2 or -25 C, the reaction vessel containing the reagents and the solvent were cooled prior to mixing together. The reactions were followed by TLC (CH2Cl2-EtOAc, 20:1). The hydrolysis was carried out in situ by adding a mixture of THF and 10% aq HCl (3:1, 1 mL) with vigorous stirring for 15-20 min. The reaction mixture was transferred to separatory funnel, diluted with H2O (10 mL), and extracted with CH2Cl2 (3 × 10 mL). The combined extracts were dried (MgSO4), concentrated, and the product was isolated by column chromatography. The racemic standards were obtained by the same procedure using 1 equiv of K2CO3 as catalyst. After the completion of the reaction, the mixture was separated from K2CO3, hydrolyzed, and purified in the same manner.

The synthetic route of 1462-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; ?ari, Sergei; Metsala, Andrus; Kudrjashova, Marina; Kaabel, Sandra; Jaerving, Ivar; Kanger, Tonis; Synthesis; vol. 47; 6; (2015); p. 875 – 886;,
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Application of 40640-98-0, The chemical industry reduces the impact on the environment during synthesis 40640-98-0, name is Ethyl 3-(4-bromophenyl)propanoate, I believe this compound will play a more active role in future production and life.

A mixture of a 60% suspension of sodium hydride in mineral oil (4.8 g, 120 mmol) in N, N-dimethylformamide (50 mL) at about 5 C was treated with diethyl malonate (36.4 mL, 240 mmol). The mixture was stirred for about 5 minutes, slowly treated with a solution of 4- bromobenzyl bromide (20.0 g, 80 mmol) in N, N-dimethylformamide (20 mL), stirred at room temperature overnight, diluted with water, and extracted with ethyl acetate. The combined organic extracts were dried (MgS04), filtered, and concentrated under high vacuum. The residue was dissolved in a mixture of acetic acid (46 mL), water (30 mL), and concentrated sulfuric acid (13 mL) and was heated to reflux for 18 hours. The reaction mixture was cooled, concentrated under high vacuum, and diluted with water. The formed crystalline solid was collected by filtration, washed with water and diethyl ether, and was dried under high vacuum to provide the desired product. MS (DCI-NH3) : m/z 246,248 (M+NH4) +.

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 3-(4-bromophenyl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; MAKOTO, Aoyama; WO2005/95387; (2005); 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. 55954-25-1, name is Methyl 2-(2,4-Dimethoxyphenyl)acetate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-(2,4-Dimethoxyphenyl)acetate

General procedure: To a stirred solution of acid 9 (320 mg, 1.76 mmol) 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 under vacuum. The crude product acid chloride was directly used for the next reaction without further purification. A solution of compound 1114 (554 mg, 2.64 mmol) in THF (6 mL) was added at -78 C to a freshly prepared solution of LDA, prepared from n-BuLi (2.5 M in THF, 1.44 mL, 3.52 mmol) and i-Pr2NH (0.49 mL, 3.52 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 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 12 (500 mg, 76%) as yellowish oily compound.

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; Pahari, Pallab; Saikia, Ujwal Pratim; Das, Trinath Prasad; Damodaran, Chendil; Rohr, Juergen; Tetrahedron; vol. 72; 23; (2016); p. 3324 – 3334;,
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Synthetic Route of 6065-54-9, These common heterocyclic compound, 6065-54-9, name is Dimethyl 2,2-dimethylmalonate, 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.

Step 2: 2.63 g Mg in 75 ml anhydrous THF are preheated to 55C, treated with 20 mg iodine and 20 mg methyl iodide, 25.7 g of 5-bromo-7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran (see below) are added maintaining reflux of the reaction, and the reaction is heated to reflux for 3 h until most of the Mg disappeared. 20 g dimethyl dimethylmalonate are solved in 40 ml anhydrous THF, cooled to – 6OC, and the freshly prepared Grignard reagent is added drop wise over 1 h at this temperature. The reaction is allowed to warm to 5C and quenched with 250 ml saturated aqueous ammonium chloride solution. The reaction is extracted with ether twice, the combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The crude product may contain some unreacted dimethyl dimethylmalonate, which could largely be distilled off under vacuum. The crude product is used for the cyclisation reaction without further purification.;

Statistics shows that Dimethyl 2,2-dimethylmalonate is playing an increasingly important role. we look forward to future research findings about 6065-54-9.

Reference:
Patent; NYCOMED GMBH; SCHLEMMINGER, Imre; SCHMIDT, Beate; FLOCKERZI, Dieter; TENOR, Hermann; ZITT, Christof; HATZELMANN, Armin; MARX, Degenhard; BRAUN, Clemens; KUeLZER, Raimund; HEUSER, Anke; KLEY, Hans-Peter; STERK, Geert Jan; WO2010/55083; (2010); A1;,
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Synthetic Route of 1126-46-1, 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. 1126-46-1, name is Methyl 4-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 8 Cross Coupling with a Zincate as the Nucleophile A solution of EtMgBr (3 M in Et2O, 0.9 mL) is added to a solution of Et2Zn (3 M in toluene, 1 mL) at -78 C. After stirring for 15 min, the resulting cold solution of the zincate is added dropwise to a solution of methyl 4-chlorobenzoate (354 mg, 2.10 mmol) and Fe(acac)3 (36 mg, 0.1 mmol) in THF (6 mL) and NMP (0.5 mL) at 0 C. causing a spontaneous color change from yellow to brown-black. Standard extractive work up followed by flash chromatography affords 4-ethylbenzoic acid methyl ester (93%) the analytical and spectroscopic data of which are identical to those of a commercial sample.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-chlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Furstner, Alois; Leitner, Andreas; Mendez, Maria; US2003/220498; (2003); A1;,
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Reference of 10328-87-7, 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. 10328-87-7, name is Methyl 2,3-Dichlorophenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

Step A: Preparation of Methyl 2-(2,3-dichlorophenyl)-2- methylpropanoate; [0472] A solution ofNaH (2.87 g, 71.8 mmol) in DMF (100 mL) was cooled to 00C. A solution of methyl 2-(2,3-dichlorophenyl)acetate (5.24 g, 23.9 mmol) in DMF(50 mL) was added dropwise, and the resulting mixture was stirred for 5 minutes. A solution of MeI (4.36 mL, 69.8 mmol) in DMF (50 mL) was then added to the reaction. After 10 minutes, the mixture was allowed to warm to 25C and the reaction was stirred for 16 hours. The mixture was diluted with 10% HCl(aq) (150 mL), and the resulting mixture was extracted with EtOAc (2×200 mL) and washed with 10% HCl(aq) (100 mL), deionized water (2×150 mL), and brine (100 mL). The organic layer was dried over MgSO4 and concentrated and dried in vacuo to give 7.06g crude product. The crude product was purified by flash column chromatography (silica, 0-50% DCM in hexane) to give the title compound (5.53 g). MS m/e = 247 (M+H)+.

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

Reference:
Patent; AMGEN INC.; WO2008/76427; (2008); A2;,
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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. 39495-82-4, name is Ethyl 5-methylhex-5-enoate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl 5-methylhex-5-enoate

A 100-mL RBF with magnetic stirrer,was flame-dried under vacuum and back-filled with a nitrogen atmosphere, then chargedwith Ethyl 5-methyl-5-hexenoate (1.5 g, 9.60 mmol) and dry DCM (30 mL). The solutionwas cooled to -78 C before the dropwise addition of diisobutylaluminium hydride (10.37mL, 1.01 M in hexanes). The mixture was stirred at this temperature for 1 h, then excessDIBAL-H was quenched by the addition of 1.0 M HCl (aq) (10 mL). Dichloromethane(30 mL) was added and the solution was warmed to 23 C and the biphasic mixture wasseparated. The Organic layer was washed with 1.0 M HCl (aq) (15 mL), the aqueouslayers were combined and extracted with DCM (2 x 15 mL). All organic layers were combined and pushed through a plug of Celite, washing with DCM (2 x 10 mL). TheDCM solution containing 5-methylhex-5-enal was transferred to a 250-mL RBF,equipped with a magnetic stirrer and dried with MgSO4 before the addition of N,Ndimethylhydrazine(1.15 g, 19.2 mmol). This mixture was stirred for 4 h at 23 C, filtered,concentrated in vacuo and purified by vacuum transfer distillation (0.5 torr) to yield 1.22g of the title compound as a colorless 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:
Article; Mickelsen, Ky; Zabawa, Sean; Livinghouse, Tom; Synlett; vol. 29; 2; (2018); p. 181 – 184;,
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Reference of 57625-74-8, 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. 57625-74-8, name is Methyl 2-methyl-2-phenylpropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 250-ML THREE-NECKED FLASK there were placed 2.5 g of 2-PHENYL-2-METHYL propionic acid methyl ester and 2.4 g of zinc cyanide and 100 ml of tetrachloroethane. A strong flow of hydrogen chloride was introduced into the flask with intense stirring during 4 hours. The flask was cooled down with an ice bath and 4.8 g of finely divided aluminium chloride were added in one dose with continued intense stirring. The stirring continued for another thirty minutes and the flask was placed onto an oil bath where it was gradually heated up to the temperature of 70 C. Further on, the mixture was kept at the given temperature for three hours. After cooling with running water, the contents of the flask were poured onto crushed ICE/15M1 conc. HCI. The reaction mixture was left to stand overnight. Then it was transferred to the flask where it was REFLUXED for three hours and after cooling, it was divided in a separatory funnel. The organic layer was separated; the aqueous layer was extracted with 15 mi of TETRACHLOROETHANE. The combined organic extracts were washed with water, with 10% sodium carbonate and dried over sodium sulphate. The solvent was distilled off until 1/3 of the volume and the product was filtered through a short column of silica gel. 2. 1 G of the product were obtained having 92.6% GC purity.

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-methyl-2-phenylpropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ZENTIVA, A.S.; WO2004/43922; (2004); 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 139911-28-7 as follows. Computed Properties of C9H8BrFO2

Example 2 – ethyl 2-cyano-5-fluorobenzoateZinc cyanide (26.5 g; 0.225 mol) and Pd2(dba)3 (1.9 g; 3.4 mmol) were added to a solution of ethyl 2-bromo-5-fluorobenzoate (27.9 g; 0.112 mol) in DMF (71 ml). Triphenyl phosphine (2.9 g; 1 1 mmol) was added and then the reaction mixture was stirred at 130C under nitrogen atmosphere for 4 hours. The mixture was poured out into H2O (300 ml) and then extracted with EtOAc (200 ml). The organic layer was separated, washed with H2O (2 x 100 ml), brine (100 ml), dried (MgS04), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: hexanes/ EtOAc (5/1, v/v)). The product fractions were collected and the solvent was evaporated.Yield: 20 g (93%; orange solid).

According to the analysis of related databases, 139911-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELANCO ANIMAL HEALTH IRELAND LIMITED; THURING, Johannes, Wilhelmus J.; WO2012/112345; (2012); A1;,
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