Tag: M.W=200-300

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. 20026-96-4, name is Ethyl 3-(4-chlorophenyl)propiolate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

b) 1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid (IIa) At r.t., a solution of N-(methoxymethyl)-N-(phenylmethyl)-N-(trimethylsilyl)methyl amine (116.8 g, 0.49 mol) in CH2Cl2 (260 ml) was added dropwise over 90 min to a stirred solution of (4-chloro-phenyl)-propynoic acid ethyl ester (72.0 g, 0.34 mol) and trifluoroacetic acid (2.5 ml, 0.03 mol) in CH2Cl2 (350 ml). The reaction mixture was stirred at 25 C. overnight and afterwards evaporated to dryness. The residue was dissolved in dioxane (0.8 l); an aqueous solution of NaOH (91.0 ml, 1.02 mol, 3 eq.) was added, and the resulting emulsion was stirred at r.t. for 48 h. The low boiling organic solvent was removed under vacuum, water (0.9 l) was added, and the aqueous layer was separated and washed with TBME (1 l). The aqueous layer was then acidified to a pH value of 2.5 by addition of 25% HCl. The resulting suspension was stirred overnight; the white precipitate was filtered off, washed with water and ethanol and dried under high vacuum to yield 62.0 g (60%) of IIa as a white solid. ES-MS m/e: 312.4 (M-H+).

The synthetic route of 20026-96-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-Emery, Fabienne; Puentener, Kurt; Ratni, Hasane; US2010/152462; (2010); A1;,
Ester – Wikipedia,
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Application of 76008-73-6, 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. 76008-73-6, name is Ethyl 5-bromo-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a) (+/-)-2-Chloro-5-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinyl]-benzoic acid, ethyl ester Prepared as described in Example 5a) using 5-bromo-2-chloro-benzoic acid, ethyl ester (0.50 g), 3-pyrrolidinyl-carbamic acid 1,1-dimethylethyl ester (0.42 g), cesium carbonate (0.86 g), palladium (II) acetate (21 mg) and (R)-BINAP (88 mg) and toluene (3 ml) to afford the subtitle compound as an oil (0.25 g). MS (APCI+ve) 311/313 (M-BOC)+

The synthetic route of Ethyl 5-bromo-2-chlorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US6492355; (2002); B1;,
Ester – Wikipedia,
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Some common heterocyclic compound, 64321-95-5, name is Methyl 2-amino-3-(trifluoromethyl)benzoate, molecular formula is C9H8F3NO2, 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. Quality Control of Methyl 2-amino-3-(trifluoromethyl)benzoate

To a stirred solution of No.105 methyl 2-amino-3-(trifluoromethyl)benzoate (IV-34, 3.6 g, 16.4 mmol) in No.107 CH3CN (22 mL) was added No.108 HBr (48% (aq), 20.3 mL) dropwise at 0C. over 10 min. Then, No.71 NaNO2 (1.25 g, 18.1 mmol) in No.21 water (5 mL) was added dropwise over 1 h at 0C. with vigorous stirring. After addition, the solution was stirred for 5 min at 0C. followed by the addition of No.109 CuBr (2.71 g, 18.9 mmol) in portions over 30 min. The mixture was heated at 70C. for 1 h then cooled again to 0C. before being diluted with water (40 mL) and extraction with EtOAc (350 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried (Na2SO4), concentrated to dryness under reduced pressure, and chromatographed (ethyl acetate/hexanes, 1:9) to afford a clear No.96 oil (3.47 g, 75%). 1H NMR (500 MHz, CDCl3) delta 7.74 (dd, J=8.0, 1.7 Hz, 1H), 7.69 (dd, J=7.7, 1.7 Hz, 1H), 7.43 (t, J=7.8 Hz, 1H), 3.92 (s, 3H). 13C NMR (126 MHz, CDCl3) delta 166.77, 136.82, 133.04, 131.53 (q, J=31.0 Hz), 129.78 (q, J=5.6 Hz), 127.38, 122.77 (q, J=273.8 Hz), 118.56, 52.93. 19F NMR (376 MHz, CDCl3) delta -62.78 (s, 3F). HRMS [M+H]+ Calcd for C9H6BrF3O2 282.9576; found 282.9575.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64321-95-5, its application will become more common.

Reference:
Patent; Northwestern University; Silverman, Richard B.; Le, Hoang V.; McLeod, Rima L.; Hawker, Dustin D.; (53 pag.)US2018/98952; (2018); A1;,
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. 20610-77-9, name is 4-Aminophenyl 4-aminobenzoate, A new synthetic method of this compound is introduced below., name: 4-Aminophenyl 4-aminobenzoate

4.56 g of 4-aminophenyl 4-aminobenzoate (20.0 mM) were suspended in 140 ml of water and 25 ml of hydrochloric acid 37 %. The suspension was cooled to 3 C and a solution of 2.83 g of sodium nitrite (41.0 mM) in 10 ml of water was added dropwise. When the addition was complete, the mixture was stirred for 1 h at 3C, then the excess of nitrite was destroyed by addition of ca. 0.5 g of amidosulfonic acid and the mixture was stirred for further 10 min. This diazo-solution was added to a solution of 5.73 g of 1-naphthylamine (40.0 mM) in 40 ml of ethanol at 5-10C. When addition was complete, the coupling mixture was stirred for 1 h at 3 C, then 37.0 g of potassium acetate were added and stirring was continued for 0.5 h. The pH of this mixture was then adjusted to pH = 7 by addition of ammonia solution 26 %. The mixture was poured onto 800 ml of ice-water and the dark precipitate was filtered off, washed with water and dried to give 17.60 g of dark crystals. These crystals were boiled for 1 h in 150 ml of methanol, the formed suspension was cooled to room temperature and the solid was filtered off, washed with methanol and dried to give 6.60 g (12.3 mM, 61 %) of 4-[(E)-(4-amino-1-naphthyl)diazenyl]phenyl 4-[(E)-(4-amino-1-naphthy)diazenyl]benzoate as dark 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:
Patent; Rolic AG; EP1593713; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 871224-19-0, 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. 871224-19-0, name is Methyl 3-bromo-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of methyl 3-bromo-2-chlorobenzoate (2.3 g, 9.27 mmol) in 1,4-dioxane (20 mL) at room temperature were added (Bpin)2 (3.5 g, 13.91 mmol), KOAc (2.7 g, 27.8 mmol) and Pd2(dppf).CH2Cl2 (0.34 g, 0.46 mmol) and degassed with argon for 5 min. The resulting mixture was maintained at 100 C. for 16 h. The reaction mixture was filtered through celite pad and the filtrate was concentrated under reduced pressure to get methyl 2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (5 g crude compound) as a dark brown semi-solid. The crude product was used for the next step without purification.

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-bromo-2-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Polaris Pharmaceuticals, Inc.; WEBBER, Stephen E.; ALMASSY, Robert J.; (75 pag.)US2018/65917; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 37555-99-0, These common heterocyclic compound, 37555-99-0, name is Diethyl 2-ethoxymalonate, 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.

Part A Preparation of mono-ethyl ethoxymalonate Diethyl ethoxymalonate (10.08 grams, 0.05 mole), prepared as described in Example LXVII, Part B, was saponified with potassium hydroxide (2.77 grams, 0.05 mole) in a mixture of 200 milliliters of ethanol and 0.88 gram (0.05 mole) of water and worked up under conditions similar to those described in Example LIX giving 4.32 grams (0.02 mole) of mono-ethyl ethoxymalonate as a residue product. NMR analysis of the product indicated the following: ‘H NMR(CDCl3) delta1.13-1.49(2xt, 6H, 2*CH3), 3.51-3.95(q, 2H, ether CH2 O), 4.10-4.50(q, 2H, ester CH2 O), 4.53(s, methine CH), 6.95(s, COOH) ppm.

The synthetic route of 37555-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Nederland B.V.; US5123951; (1992); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 139911-28-7, 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. 139911-28-7, name is Ethyl 2-bromo-5-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 2-(2-Methyl-4-fluorophenyl)-5-fluorobenzoate Tetrakis(triphenylphosphine)palladium(O) (0.02 eq, 0.31 g) was added to a vigorously stirred solution of ethyl 2-bromo-5-fluorobenzoate (1.0 eq, 3.3 g, 0.013 mol) and 2-methyl-4-fluorophenylboronic acid (1.2 eq, 0.016 mol, 2.4 g) in 45 mL of toluene, 22 mL of 2M aqueous sodium carbonate, and 11 mL of ethanol and the mixture was refluxed for 9 h. The cooled reaction mixture was poured into 50 mLeach of water, ammonium hydroxide, and 2M aqueous sodium bicarbonate and then filtered through Celite. The filtrate was extracted with ethyl acetate an the organics were dried (MgSO4) and concentrated to yield 3.9 g of a yellow oil. Chromatography (silica gel, 20% ethyl acetate/hexane) gave 3.4 g (92%) of product as a light colored oil. 1 H NMR (CDCl3, 60 mHz) delta7.7 (dd, 1H), 7.5 (m, 1H), 7.25-6.75 (m, 4H), 4.0 (q, 2H), 2.0 (s, 3H), 1.0 (t, 3H); IR (CDCl3 solution) 3130, 2220, 1700, 1450, 1080 cm-1; MS m/z 276 (M+), 201 (base peak).

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-bromo-5-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Alcon Laboratories, Inc.; US4864028; (1989); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 1070-64-0 as follows. Formula: C10H18Cl2O2

To a solution of ethyl 6,8-dichlorooctanoate (6.01 g, 25 mmol) in 95% ethanol (10mL)was added sodium hydroxide (2 g, 50 mmol) and water (38 mL). The mixture was heated to 50 C for 1.5 h and the aqueous disodium diselenide (prepared from 3.95 g selenium powder19) was then added dropwise at 65 C. After stirring for 2 h, the mixture was cooled to 40 C and activated carbon (8 g) was then added. After stirring for 0.5 h, the mixture was filtered, and the ethanol was distilled off under reduced pressure (caution: the temperatureof the filtrate must not exceed 50C). Water (400 mL) was added to the residue and the mixture was cooled to 0 C. A solution of 10% hydrochloric acid was then added dropwise till pH = 1, resulting in the formation of a solid product. The solid was filtered and washed thoroughly with water.

According to the analysis of related databases, 1070-64-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xu, Feng; Yang, Zhen-Zhen; Zhang, Shi-Jie; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 188; 10; (2013); p. 1312 – 1319;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 3195-24-2,Some common heterocyclic compound, 3195-24-2, name is Diethyl 2,2-diallylmalonate, molecular formula is C13H20O4, 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.

A study of the RC of several substrates has also been carried out. Reactions were run in toluene at 80C in the presence of 1 to 5 mol% of cis-2, the higher catalyst loading being only necessary for the formation 17 featuring a tetra-substituted double bond (Table 4 below, entry 3). The RCM of unhindered malonate derivatives was achieved in short reaction times (less than 1 hour) and in good yields. Indeed, di- and tri-substituted cyclopentenes 15 and 9 were obtained in quantitative yields (entries 1 & 2). Nevertheless, highly constrained substrate 16 could not be cyclized with full conversion, even after 24h at 80C, and was isolated in 70% yield (entry 3). Finally, 6- and 7-membered rings 19 and 21 were obtained in respectively 96 and 87% yield, and no increase in reaction time compared to 5-membered ring 15 (entries 4 & 5). Of note, a dilution to 0.05M was necessary to obtain 21 without observing parallel formation of polymers. We next attempted the RCM of cyano analogues 24 and 26 (entries 6 & 7). Non-hindered cyclopentene 23 was isolated in good yield (88%), indicating that the presence of potentially chelating cyano groups was not detrimental to catalysis. Nevertheless, cis-2 was unable to promote the formation of 25, the starting material remaining unreacted. Tosylamine-based olefins were next investigated. The cyclization of these compounds was found very efficient regardless of hindrance and ring size. Indeed, 5-, 6- and 7-membered compounds 7, 27 and 29 were isolated in excellent yields (entries 8-10), albeit a slight increase in reaction time was needed for larger rings. Catalyst loading of only 2 mol% was necessary to achieve the cyclizations of 30 and 32 to obtain tetrasubstituted 5- and 6-membered rings 31 and 33 in good yields (entries 11 & 12), even so 5 hours of reaction were needed for dihydropyrrole 31. Amide and ether-based substrates were also efficiently cyclized, with yields spanning from 80% to 99% (entries 13-17). Increasing the ring size to 6 or 7 members was not detrimental, as products 39, 41 and 43 were obtained excellent yields in less than 1 hour (entries 15-17). From this study, catalyst c/s-2 seemed to be highly tolerant to functionalities and able to effect RCM easily.This utility of the complexes of the invention is illustrated further in figure 4 which shows RCM of compound 30 (table 4 entry 11 ) in toluene at 80C carried out with a range of Ru complexes. Trans or cis-2 both rapidly produce a high conversion whereas prior art complexes Hov-ll, G-ll, M2 (structures shown in Scheme 1 ) and M31 (which is the pyridine complex 1 in scheme 2) did not produce any better than about 60% conversion (complex M2) under these conditions

The synthetic route of 3195-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; CAZIN, Catherine; WO2011/117571; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 223519-11-7, 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. 223519-11-7 name is Methyl 3-amino-5-bromo-4-methylbenzoate, 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.

Methyl 3-amino-5-bromo-4-methylbenzoate (1.15 g, 4.62 mmol), triethylamine (1.28 mL, 9.21 mmol) and dichloromethane (20 mL) were added to a 100 mL two-neck flask, then trifluoroacetic anhydride (0.79 mL, 5.6 mmol) was added dropwise at 0C. The reaction mixture was stirred for 1 h at rt. The mixture was concentrated in vacuo to remove solvent. To the residue was added saturated brine (80 mL) and ethyl acetate (80 mL), and the resulting mixture was partitioned. The organic phase was washed with saturated brine (40 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound as a yellow solid (1.5 g, 95%).MS (ES-API, pos. ion) m/z: 341.0 [M + 2]t

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-5-bromo-4-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; YANG, Xinye; HUANG, Changwei; MA, Facheng; ZHANG, Ji; WANG, Xiaojun; ZHANG, Yingjun; (162 pag.)WO2017/36404; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics