Tag: M.W=200-300

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 721-63-1 as follows. Computed Properties of C11H11F3O2

General procedure: To a stirred solution of phenyl acetic acid ethyl ester 1a (1 g, 6.09 mmol) in THF (10 mL) was added LiHMDS (9.1 ml, 1 M sol. in THF, 7.31 mmol) at -78 C and the reaction mixture was stirred at this temperature for 30 min. Ethyl-1-imidazole carboxylate 2 (1.2 g, 9.146 mmol) in dry THF (3 ml) was added drop wise to the reaction mixture at -78 C and stirred at rt for 3 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layer was washed with water, saturated brine solution, and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was chromatographed on a silica gel column. Elution with 4% ethyl acetate/pet ether gave the pure compound 3a (1.1 g, 81% yield) as a colorless liquid.

According to the analysis of related databases, 721-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Behera, Manoranjan; Venkat Ragavan; Sambaiah; Erugu, Balaiah; Rama Krishna Reddy; Mukkanti; Yennam, Satyanarayana; Tetrahedron Letters; vol. 53; 9; (2012); p. 1060 – 1062;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 135484-83-2,Some common heterocyclic compound, 135484-83-2, name is Methyl 2-amino-4-bromobenzoate, molecular formula is C8H8BrNO2, 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 toluene 12mL solution of methyl 2-amino-4-bromobenzoate 1.2g were added 1-fluoro-4-iodobenzene 1.5mL, cesium carbonate 3.4g, palladium acetate 12mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, palladium acetate 12mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32mg were added to it, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, water was added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 1.0mol/L hydrochloric acid and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B (spherical type), eluent; hexane:ethyl acetate=10:1] to give methyl 4-bromo-2-(4-fluoroanilino)benzoate 0.20g of pale yellow solid. 1H-NMR(DMSO-d6) delta value: 3.86(3H,s),6.94(1H,dd,J=8.6,1.7Hz),7.04(1H,d,J=1.7Hz),7 .24-7.35(4H,m),7.80(1H,d,J=8.6Hz),9.27(1H,s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-amino-4-bromobenzoate, its application will become more common.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1860098; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 49851-36-7, 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. 49851-36-7, name is Methyl 2-(2-aminophenyl)acetate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

TEA (0.276 ml_, 1 .984 mmol) was added to a mixture of 3-bromobenzoic acid (199 mg, 0.992 mmol) and HATU (415 mg, 1 .091 mmol) in DMF at 23 C. In a separate vial, methyl 2-(2- aminophenyl)acetate hydrochloride (CAS 49851 -36-7) (200 mg, 0.992 mmol) was stirred with TEA (0.276 ml_, 1 .980 mmol) in DMF (0.5 ml_). After 5 min, the solution of methyl 2-(2- aminophenyl)acetate hydrochloride (200 mg, 0.992 mmol) was added to the 3-bromobenzoic acid (199 mg, 0.992 mmol) mixture and the resulting mixture was stirred at rt for 30 min. The reaction mixture was diluted with EtOAc and washed with water. The aqueous layer was extracted with EtOAc. The combined organics were washed with 5% aq LiCI, dried (Na2S04) and concentrated. The resulting residue was purified by silica gel chromatography (EtOAc- heptanes 0-60%) to provide the title compound. MS (ESI+) m/z 348.0, 350.0 (M+H).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-(2-aminophenyl)acetate hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BELANGER, David B.; FLOHR, Stefanie; GELIN, Christine Fang; JENDZA, Keith; JI, Nan; LIU, Donglei; LORTHIOIS, Edwige Liliane Jeanne; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; POWERS, James J.; RANDL, Stefan Andreas; ROGEL, Olivier; VULPETTI, Anna; YOON, Taeyoung; WO2015/9977; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 185312-82-7, name is Methyl 4-bromo-2-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 185312-82-7

Preparation Example 10-1 To a solution of methyl 4-bromo-2-chlorobenzoate (1.25 g) in N,N-dimethylformamide (10 ml) was added sodium thiomethoxide (459 mg) under ice-cooling and the mixture was stirred for 2 hr. To the reaction mixture was added 1N hydrochloric acid and the resulting product was extracted 3 times with diethyl ether. The organic layers were combined, washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was applied to silica gel column chromatography (hexane/ethyl acetate=10/1) to give methyl 2-chloro-4-(methylthio)benzoate (835 mg) as a colorless oil. 1H-NMR(CDCl3): 2.49(3H, s), 3.90(3H, s), 7.11(1H, d, J=8Hz), 7.23(1H, s), 7.78(1H, d, J=8Hz).

According to the analysis of related databases, 185312-82-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; EP1142879; (2001); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 14062-30-7, name is Ethyl 2-(3-bromophenyl)acetate, molecular formula is C10H11BrO2, 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. Recommanded Product: 14062-30-7

(3-Cyano-phenyl)-acetic acid ethyl ester A mixture of (3-bromo-phenyl)-acetic acid ethyl ester (9.15 g, 37.6 mmol), copper cyanide (5.06 g, 56.5 mmol), and 1-methyl-2-pyrrolidinone (80 mL) was placed into an oil bath heated at 120 C. behind a protective shield. The reaction was heated to 200 C. for 1 h and additional copper cyanide (spatula tip) was added. After heating for an additional 0.5 h, the reaction was cooled to room temperature. The reaction was diluted with EtOAc and the organic solution was washed with water/ammonium hydroxide solution (2:1 v/v) until the aqueous solution was no longer blue. The organic solution was washed with brine, dried (MgSO4), filtered, and concentrated. Flash chromatography (9:1 hexanes:EtOAc) provided (3-cyano-phenyl)-acetic acid ethyl ester (6.31 g) as a clear oil which solidified on standing. 1H NMR (400 MHz, CDCl3) delta7.57-7.50 (m, 3H), 7.42 (m, 1H), 4.15 (q, 2H), 3.63 (s, 2H), 1.24 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14062-30-7, its application will become more common.

Reference:
Patent; Pfizer Inc.; US6344485; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

59247-47-1, name is tert-Butyl 4-bromobenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of tert-Butyl 4-bromobenzoate

(2S,3’S)-2-Methyl-[1,3′]bipyrrolidinyl dihydrochloride (8) (1.1 g, 4 mmol) was treated with NaOt-Bu (1.1 g, 2equiv) in MeOH (30 mL), filtered, and concentrated. To this flask was added tert-butyl-4-bromo-benzoate (9) (1.0 g, 3.89 mmol), sodium tert-butoxide (538 mg, 5.6 mmol), tris(dibenzylideneacetone)-dipalladium-(0) (35 mg, 0.039 mmol), BINAP (72 mg, 0.116 mmol), and toluene (40 mL) under nitrogen. The reaction flask was heated to 80 °C (external) for 24 h with stirring until the starting material was completely consumed as judged by TLC analysis. The mixture was cooled to room temperature, taken up in DCM (50 mL), filtered, and concentrated. The crude product was then purified by a silica gel flash chromatography eluted with 0-5percent of 7 N NH3/MeOH in DCM to get 1.02 g (80percent) of the title compound as a yellow oil. LCMS: RT = 2.23 min, MS: 331 (M+H+). 1H NMR (300 MHz, CDCl3) delta 7.87 (d, J = 8.7 Hz, 2H), 6.49 (d, J = 8.7 Hz, 2H), 3.6-3.23 (m, 5H), 3.01 (m, 1H), 2.78 (m, 1H), 2.55 (q, J = 8.4 Hz, 1H), 2.22-1.43 (m, 13H), 1.14 (d, J = 6.3 Hz, 3H).

The synthetic route of 59247-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Zhongli; Hurst, William J.; Hall, Daniel; Hartung, Ryan; Reynolds, William; Kang, Jiesheng; Nagorny, Raisa; Hendrix, James A.; George, Pascal G.; Bioorganic and Medicinal Chemistry; vol. 23; 3; (2015); p. 429 – 438;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 23062-51-3, name is Methyl 4-bromobicyclo[2.2.2]octane-1-carboxylate, molecular formula is C10H15BrO2, 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. Computed Properties of C10H15BrO2

Methyl 4- bromobicyclo [2.2.2]octane-l-carboxylate (17.0 g, 69.0 mol) was refluxed in aqueous sodium hydroxide solution (1500 mL, 1 %) for 24 h. After cooling, the reaction solution was acidified with hydrochloric acid (6 N, 100 mL) and extracted with diethyl ether (6 x 500 mL). The combined ether layers were dried over magnesium sulfate and concentrated to afford the title compound (10.4 g, 61.1 mmol, 89 % yield), which was used in the next step without further purification. MS (ESI) m/z 169.2 [M-H]~.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 23062-51-3, its application will become more common.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 82702-31-6, 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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of methyl 3-bromo-4-fluorobenzoate (4.22 g, 18.10 mmol) and Example 1g (2.727 g, 19.46 mmol) in dimethyl sulfoxide (18.10 mL) was treated with cesium carbonate (9.28 g, 28.5 mmol) . The reaction mixture was heated at about 80 C for about 2 hours and cooled to ambient temperature. Water (50 mL) was added, and the reaction mixture was stirred for 10 minutes. The reaction mixture was extracted with methyl tert-butyl ether (1x 100 mL, then 2×50 mL) . The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 100% heptanes to 30ethyl acetate: heptanes) to provide the title compound as a white solid (5.29 g, 15.0 mmol, 83% yield) .

The synthetic route of Methyl 3-bromo-4-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; COWART, Marlon; FIDANZE, Steven; HASVOLD, Lisa; LIU, Dachun; MCDANIEL, Keith; PRATT, John; SHEPPARD, George; WANG, Le; (241 pag.)WO2018/68283; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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 69812-51-7, Product Details of 69812-51-7

General procedure: To a solution of 23 (313 mg, 1 mmol) in DMF (1 mL), was addedtriethylamine (210 mg, 2.05 mmol), methyl 4-chlorosulfonyl benzoate27c (235 mg, 1 mmol) and 4-dimethylaminopyridine (10 mg). Themixture was stirred at rt for 4 h. The solvent was removed and the residuewas purified by a silica column with CHCl3 and MeOH to afford356 mg of 24f as a white solid in 75% yield. TLC Rf 0.13 (CHCl3/MeOH,40:1); 1H NMR (DMSO-d6) delta 1.25 (s, 9H, Piv), 2.61 (s, 3H, NCH3), 3.91(s, 3H, OCH3), 4.21 (s, 2H, NCH2), 6.28 (s, 1H, 5-H), 7.95 (d,J=8.0 Hz, 2H, Ph), 8.18 (d, J=8.0 Hz, 2H, Ph), 10.85 (s, 1H, exch,PivNH), 11.66 (s, 1H, exch, NH), 11.88 (s, 1H, exch, NH).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Xiang, Weiguo; Dekhne, Aamod; Doshi, Arpit; O’Connor, Carrie; Hou, Zhanjun; Matherly, Larry H.; Gangjee, Aleem; Bioorganic and Medicinal Chemistry; vol. 27; 23; (2019);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 1132-95-2, 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 1132-95-2 as follows.

The compound (103 mg) produced in production step 11-1 was dissolved in 2.0 mL of N,N-dimethylformamide. Cyclohexanone di-i-propyl acetal (58 muL) and 12.4 mg of p-toluenesulfonic acid were added to the solution, and the mixture was allowed to react at room temperature for one hr. A saturated aqueous sodium bicarbonate solution (20 mL) was added thereto, and the resultant precipitate was collected by filtration, was washed with water, and was dried under the reduced pressure to give the title compound (103 mg, 88%). Rf value: 0.53 (chloroform: methanol = 10: 1) ESIMS: m/z 1171 [M + Na]+

According to the analysis of related databases, 1132-95-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Meiji Seika Kaisha Ltd.; Microbial Chemistry Research Foundation; EP2036917; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics