Month: July 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. 42122-75-8, name is Methyl 5-amino-2-chlorobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H8ClNO2

37.12 g (0.2 mol) was added to a 500 mL three-necked flask as shown in formula (C)2-chloro-5-amino-benzoic acid methyl ester, 100 mL hydrochloric acid and 70 mL water,Mechanically stirred, cryogenically cooled to -5-0 C, with a pale yellow solid precipitated,Dissolve 13.8 g (0.2 mol) of sodium nitrite in 20 mL of water.Then slowly added dropwise to the above three-necked flask, after the dropwise addition within 45 minutes,The light yellow solid in the three-necked flask was completely dissolved, and the solution was orange-yellow.The temperature of the reaction solution was maintained at -2-0 C. The mixture in a three-necked flask was stirred for 15 min.Then, 45.7 g (0.25 mol HBF4) of 48% tetrafluoroboric acid solution was added dropwise.After about 30 minutes, the temperature of the reaction solution is kept at 0-2 C.Stirring was continued for 2 hours. After the reaction is completed, the reaction solution is suction filtered.The residue was washed successively with dilute tetrafluoroboric acid solution, washed with 50% ethanol (50 mL) and washed with anhydrous ethanol (50 mL), and dried to give 43.2 g of pale yellow solid, yield 75.6%.

The synthetic route of 42122-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Tan Chengxia; Pei Dan; Zhang Fan; Zhang Donglin; (26 pag.)CN108997325; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 61367-07-5, A common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, molecular formula is C8H16ClNO2, 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.

(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (93.0 g) obtained in Reference Example 2(1) is dissolved in methanol (1000 ml), and thereto are added 35 % aqueous formaldehyde solution (95.4 ml), sodium acetate (39.4 g) and 10 % palladium/carbon (10 g). The mixture is then stirred at room temperature for 3.5 hours under atmospheric hydrogen pressure. The insoluble materials are removed by filtration, and the filtrate is concentrated under reduced pressure. To the resulting residue is poured 20 % aqueous potassium carbonate solution (500 ml), and the mixture is extracted with chloroform. The organic layer is dried over sodium sulfate and potassium carbonate, and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate = 2/1) to give methyl trans-4-dimethylaminocyclohexanecarboxylate (87.3 g). APCI-MS M/Z:186[M+H]+.;

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; TANABE SEIYAKU CO., LTD.; EP1582521; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 104901-43-1, 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. 104901-43-1 name is Methyl 3-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-bromo-4-methy. benzoate (50.0 g, 220 mmol) was dissolved in a mixture of 200 ml DMF, 12.5 ml water and 80 ml of tributyl amine. Cesium acetate (20.9 g, 109 mmol) was added and the flask was purged with CO gas. Pd(OAc)2 (2.45 g, 10.9 mmol) and triphenyl phosphine (28.6 g, 109 mmol) were added quickly and the flask was re-purged with CO gas. A balloon filled with CO gas was installed through the septum and the reaction was heated to 95 0C with vigorous stirring overnight. LC-MS showed a 1 :1 ratio of product to starting material. The reaction was diluted with 500 ml of toluene and extracted three times with 300 ml of a NaHCO3 solution. The combined aqueous layer was washed with 100 ml of ethyl acetate, then acidified with 1 N HCI. The resulting precipitate was filtered, washed with 100 ml of water and dried to give a solid (10.8 g, 25% yield). 1H NMR (400 MHz, DMF-O7) delta 13.53 (br s, 1 H), 8.52 (d, J= 1.9 Hz, 1H), 8.03 (dd, J = 9.9, 1.9 Hz, 1H), 7.50 (d, J = 7.9 Hz, 1H), 3.91 (s, 3H), 2.65 (s, 3H); LC/MS, tr = 1.88 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min, at 254 nm, at 50 0C), ES- MS m/z 195 (M+H). ES-HRMS m/z 193.0473 (M-H calcd for C10H9O4 requires 193.0501).

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

Reference:
Patent; PHARMACIA & UPJOHN COMPANY LLC; WO2006/18735; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 34846-90-7, The chemical industry reduces the impact on the environment during synthesis 34846-90-7, name is Methyl 3-methoxyacrylate, I believe this compound will play a more active role in future production and life.

17.5 g (100 mmol) of 4-methoxyphenylhydrazine hydrochloride, 11.6 g (100 mmol) of methoxyMethyl acrylate, and 100 mL of methanol. The reaction mixture was heated to reflux for about 6 hours. The reaction solution was quantified by liquid chromatography,and 1- (4-methoxyphenyl) -5-hydroxypyrazole Yield 79.3percent

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

Reference:
Patent; Hunan Haili Changde Agrochemical Co.,Ltd.; Hu, Zhibin; Liu, Weidong; Du, Shenghua; Huang, Chaoqun; Lan, Shilin; Xiong, Lili; Wu, Yinyin; Cheng, Chao; Wang, Yanli; (6 pag.)CN104059020; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 6091-64-1, 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. 6091-64-1, name is Ethyl 2-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of copper powder (63.5 mg, 1.00 mmol), the aryl halide (500 mumol), 2-aminoethanol (74.9 muL, 1.25 mmol), and TMSN3 (133 muL, 1.00 mmol) in DMA (1 mL) in a 15 mL test tube was stirred under an Ar atmosphere (balloon) at 95 C using a Chemistation personal organic synthesizer (EYELA, Tokyo). After complete consumption of the aryl halide was confirmed by TLC analyses or after 24 h (if the reaction was incomplete within 24 h), the mixture was diluted with EtOAc (10 mL) and then filtered through a Celite pad. The pad was successively washed with EtOAc (20 mL), H2O (25 mL), and concd aq ammonia solution (5 mL). After the two layers were separated, the aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine (20 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography with n-hexane/EtOAc or n-pentane/Et2O as the eluent.

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

Reference:
Article; Maejima, Toshihide; Shimoda, Yutaka; Nozaki, Kei; Mori, Shigeki; Sawama, Yoshinari; Monguchi, Yasunari; Sajiki, Hironao; Tetrahedron; vol. 68; 6; (2012); p. 1712 – 1722;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 57381-59-6,Some common heterocyclic compound, 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate, molecular formula is C8H6BrFO2, 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 1 (0342) To a solution of 4a (28 g, 113 mmol) in DMF (500 mL) was added naphthalene- 1,6-diol (22 g, 136 mmol) and CS2CO3 (74 g, 226 mmol). The resulting solution was stirred at 100C for 12 h, before it was poured into water and extracted with EA. The combined organic phases were dried over Na2S04. After filtration and concentration, the residue was purified by Si02 chromatography, eluting with petroleum ether: ethyl acetate (100/1-10/1) to give compound 4b (25 g, 59.5%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-bromo-2-fluorobenzoate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KOZLOWSKI, Joseph, A.; YU, Wensheng; HU, Bin; ZHONG, Bin; HAO, Jinglai; WANG, Dahai; LEI, Zhixin; (82 pag.)WO2017/184476; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 2901-13-5, 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. 2901-13-5, name is Ethyl 2-methyl-2-phenylpropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 2-(4-Formylphenyl)-2-Methylpropionate (formula II; R1 =COOEt) (alternate synthesis): Ethyl 2-phenyl-2-methylpropionate (10 g) was dissolved in 50 mL of dichloromethane and cooled to 5 C. Titanium tetrachloride (10.5 mL) and 1,1-dichloromethyl methyl ether (7.5 mL) were added and the mixture was stirred at room temperature for 60 hours. The resulting dark solution was diluted with 50 mL of dichloromethane and washed twice with 50 mL of water. The organic solution was concentrated to give an oil which was treated with 30 mL of saturated aqueous sodium bisulfite solution for 12 hours. The precipitate was collected by filtration, washed with hexane, suspended in ethyl acetate and treated with excess potassium carbonate. The organic phase was separated, dried with sodium sulfate and stripped to provide 2 g of product. Ethyl 2-[3-(1,3-Dioxolan-2-yl)-1-HydroxyPropylphenyl]-2-Methylpropionate:

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

Reference:
Patent; Sepracor Inc.; US5925761; (1999); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 394-35-4, The chemical industry reduces the impact on the environment during synthesis 394-35-4, name is Methyl 2-fluorobenzoate, I believe this compound will play a more active role in future production and life.

To methyl 2-fluorobenzoate (300 mg) in 9 mL of THF was added NaHMDS (5.2 mL, 1 M in THF) at -78°C. To this mixture was then added (4-chloro-2-fluorophenyl)acetic acid (367 mg) as solid in one portion at -78°C. The mixture was stirred at -78°C for 4 h and then quenched with 3 N HC1 at this temperature and stirred at rt for overnight. The mixture was diluted with ethyl acetate and water. The organic layer was dried and concentrated to remove solvents. The afforded residue was purified by silica gel flash chromatography (0 to 100percent EtOAc/hexane, product out at 25percent) to give the desired product 2-(4-Chloro-2-fluorophenyl)-l-(2- fluorophenyl)ethanone as white solid.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; LAN, Ping; LIU, Kun; OGAWA, Anthony; SHEN, Hong; YANG, Christine; WANG, Yuguang; BERESIS, Richard; QI, Changhe; WO2012/139495; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 61367-07-5, A common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, molecular formula is C8H16ClNO2, 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.

To a suspension of 6-chloro-8-(cyclopropylamino)-N-(3-fluoropyridin-4- yl)imidazo[l,2-b]pyridazine-3-carboxamide (0.030 g, 0.087 mmol) and DIEA (0.227 mL, 1.298 mmol) in NMP (1 mL) was added trans-methyl 4- aminocyclohexanecarboxylate, HCl (0.201 g, 1.038 mmol). The resulting suspension was heated to 120 0C in a 300W CEM Discover microwave for 60 min. The crude material was diluted with 1 mL MeOH and purified via preparatory HPLC using a YMC ODS C-18 column (30 x 250 mm) 0%-100%B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B = O, final % B = 100, gradient time 240 min, hold at 100% B 40 min, flow rate 25 mL/min. Material was redissolved in DMSO/THF and purified via preparatory HPLC using a YMC ODS C-18 column (30 x 250 mm) 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B = O, final % B = 100, gradient time 60 min, flow rate 25 mL/min, to afford methyl trans-4-((8-(cyclopropylamino)-3-((3-fluoro-4- pyridinyl)carbamoyl)imidazo[l,2-b]pyridazin-6-yl)amino)cyclohexanecarboxylate, 2TFA (0.006 g, 9.97% yield) obtained as a white foam. LC/MS, m/z 468.0 (M+l). HPLC Rt = 4.120 min. YMC S5 ODS-A column (4.6 x 50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.2% H3PO4). Solvent A: (10% MeOH, 90% H2O, 0.2% H3PO4). Gradient, start % B = O, final % B = 100, gradient time 4 min, hold at 100% 1 min, flow rate 4 mL/min. 1H NMR (500 MHz, DMSO-d6) delta ppm11.46 (1 H, s), 8.67 (1 H, d, J=2.75 Hz), 8.55 (1 H, t, J=5.91 Hz), 8.41 (1 H, d, J=5.77 Hz), 8.00 (1 H, s), 7.57 (1 H, s), 7.00 (1 H, s), 6.07 (1 H, s), 2.06 (3 H, s), 1.91 (4 H, s), 1.58 (1 H, d), 1.30 (4 H, d, J=10.45 Hz), 1.05 (2 H, d, J=I 1.27 Hz), 0.76 (2 H, d, J=4.95 Hz), 0.57 – 0.67 (2 H, m).

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; BRISTOL-MYERS SQUIBB COMPANY; WO2009/100375; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 23680-40-2, name is Methyl 3-bromopropiolate, 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 23680-40-2, SDS of cas: 23680-40-2

The product of Step A (1 1.3g, 69mmol) and f-butyl pyrrole- 1 -carboxylate (30 mL, 1 SOmmol) was combined and heated at 95 and allowed to stir at this temperature for 24 hours. The product was purified using chromatography on silica to provide compound 7OC as a yellow oil.

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

Reference:
Patent; SCHERING CORPORATION; WO2009/55331; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics