Author: Jessica.F

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. 869-10-3, name is Diethyl 2,5-dibromohexanedioate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Diethyl 2,5-dibromohexanedioate

A solution of diethyl 2,5-dibromoadipic acid (8.0 g, 0.0222 mol) in toluene (25 mL) was heated to 80C and after stopping the heating, thereto was added dropwise 2-methoxyaniline (4.1 g, 0.333 mol) over 40 min., and the mixture was stirred at 100C for 11 hours again. The reaction solution was filtered under reduced pressure and the filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to give the title compound 2.08 g as white solids. 1H-NMR (CDCl3) delta; 1.25 (6H, t, J=7.2Hz), 2.21 (4H, m), 3.71 (3H, s), 4.21 (4H, m), 4.36 (2H, m), 6.70 (1H, m), 6.82 (3H, m).

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 869-10-3.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1736467; (2006); A1;,
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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. 681128-38-1, name is Ethyl 3,3-difluorocyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H10F2O2

Preparation 32: 4-(3-chloro-5-(3,3-difluorocyclobutyl)-4,5-dihydro-1H-pyrazol-1-yl)- 2-methylbenzonitrile; Step 1 : ethyl S-O.S-difluorocvclobutvDacrylate; To a solution of ethyl 3,3-difluorocyclobutanecarboxylate (1.94 g, 11.82 mmol) in dichloromethane (40 ml_) at -78C was added diisobutyl aluminum hydride (13 ml_ of a 1.0M solution in hexanes, 13.0 mmol). The reaction was stirred at -78C for 45 min. Saturated aqueous ammonium chloride (40 ml_) was added, and the resulting mixture stirred overnight at room temperature. The biphasic mixture was filtered through celite. The organic layer was dried over sodium sulfate, filtered and concentrated to give 3,3- difluorocyclobutanecarboxaldehyde which was used immediately without further purification. To a suspension of sodium hydride, 60 wt% dispersion in mineral oil (487 mg, 12 mmol) in tetrahydrofuran at 0C was added triethyl phosphonoacetate (2.4 mL, 12.0 mmol) dropwise. After addition was complete, the mixture was allowed to warm to room temperature, and stirred until the suspension cleared (~10 min.). 3,3- difluorocyclobutanecarboxaldehyde was added as a solution in tetrahydrofuran (10 mL). The resulting solution was stirred at room temperature 4 h. Diethyl ether (40 mL) was added, and the reaction was quenched by addition of saturated aqueous ammonium chloride (20 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography eluting with a gradient of 0%-5% ethyl acetate in heptane to yield ethyl 3-(3,3- difluorocyclobutyl)acrylate (498 mg, 22%) as a yellow oil. 1 H NMR ( 400 MHz,CHLOROFORM-d) delta ppm 1.30 (3 H, t, J=7.1 Hz), 2.49 (2 H, m), 2.83 (2 H, m), 2.94 (1 H, m), 4.21 (1 H, q, J=7.2 Hz), 5.85 (1 H, dd, J=15.5, 1.3 Hz), 7.00 (1 H, dd, J=15.5, 7.3 Hz).

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 681128-38-1.

Reference:
Patent; PFIZER INC.; ARHANCET, Graciela Barbieri; CASIMIRO-GARCIA, Agustin; CHEN, Xiangyang; HEPWORTH, David; MEYERS, Marvin Jay; PIOTROWSKI, David Walter; RAHEJA, Raj Kumar; WO2010/116282; (2010); A1;,
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These common heterocyclic compound, 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, 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. Quality Control of Methyl 2-(2-bromophenyl)acetate

2-(2-Bromophenyl)-propionic acid methyl ester:[0275] In a 500 mL round bottom flask, 5.1460g (45.8603 mmol, 2.2 eq) of the potassium t-butoxide was suspended in 190 mL of clean, dry THF under N2 atmosphere. To this was added 4.7751 g (20.8456 mmol, 1.0 eq) of the methyl ester dissolved in 10 mL of THF. The solution immediately became a cloudy yellow. The reaction solution was allowed to stir for thirty minutes at room temperature. To the stirred reaction was then added 2.86 mL (48.8603 mmol, 2.2 eq) of the methyl iodide in one portion. The reaction was allowed to stir overnight at room temperature. The following morning, the reaction was diluted with 200 mL of H20. The layers were separated and the aqueous solution was extracted with EtOAc (2 x 100 mL). The organic layers were combined, washed with brine (1 x 100 mL) and dried overNa2S04. The solvent was removed under reduced pressure, yielding a deep yellow oil. The oil was taken up in EtOAc and concentrated onto Celite. The product was then purified using silica gel column chromatography, eluting a gradient of 100% heptane to 50% EtOAc in heptane. A colorless oil was isolated. LCMS (m/e): 244 (M+H); NMR (400 MHz, acetone- d6) delta ppm 1.44 (d, J=7.17 Hz, 3 H) 3.50 – 3.72 (m, 3 H) 4.20 (q, J=7.18 Hz, 1 H) 7.11 – 7.26 (m, 1 H) 7.37 (d, J=4.73 Hz, 2 H) 7.56 – 7.66 (m, 1 H).

The synthetic route of Methyl 2-(2-bromophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; JACOBS, Robert, T.; CHEN, Daitao; ORR, Matthew; PLATTNER, Jacob, J.; WO2011/116348; (2011); A1;,
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Application of 2672-58-4,Some common heterocyclic compound, 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate, molecular formula is C12H12O6, 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.

Take 8.00 g of trimesic acid methyl ester 35 oC dissolved in 80 mL of anhydrous tetrahydrofuran,Under nitrogen protection by a constant pressure funnel was slowly added dropwise to 3.00 g of lithium aluminum hydride and 300 mL of anhydrous tetrahydrofuran mixture,The dropwise addition was carried out in ice-salt bath, and the temperature was restored to room temperature after the addition was completed. The mixture was stirred at reflux for 70 oC for 24 h,The reaction was carried out under magnetically stirred ice bath-reflux integrated nitrogen protection. After the reaction, the reaction was quenched with about 100 mL of distilled water, the mixture was suction filtered, the filter cake was washed three times with 100 mL of methanol, and the filtrate was distilled under reduced pressure ,80 oC vacuum drying, 5.12 g are tribenzyl alcohol(96% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Trimethyl benzene-1,3,5-tricarboxylate, its application will become more common.

Reference:
Patent; Jilin Chemical College; Gao Wenxiu; Wang Jisi; Lou Dawei; Yu Dandan; Zhang Zhihui; Zhang Hao; (9 pag.)CN107501043; (2017); A;,
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Related Products of 14920-81-1, 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. 14920-81-1 name is Methyl 2,6-dimethylbenzoate, 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.

EXAMPLE 2; Methyl 2-bromomethyl-6-methyl-benzoate; To a solution of methyl 2,6-dimethyl-benzoate (22.0 g, 134 mmol, example 1) in CCl4 (250 mL) is added N-bromo-succinimide (19 g, 107 mmol) followed by benzoyl peroxide (1.0 g, 4.0 p mmol). The resulting solution is warmed to reflux and stirred at this temperature for 20 min. The reaction mixture is then allowed to cool before being diluted with ether (200 mL), filtered and concentrated. The residue is purified by flash chromatography (silica, 4% acetone in hexanes) to give the title compound. This product (approx. 85% purity, remainder is methyl 2,6dimethyl benzoate) is used without further purification. MS (EI) 242, 244 (M+, Br pattern).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2,6-dimethylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Aventis Pharma Deutschland GmbH; US7005440; (2006); B1;,
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Reference of 24393-53-1,Some common heterocyclic compound, 24393-53-1, name is (E)-Ethyl 3-(4-bromophenyl)acrylate, molecular formula is C11H11BrO2, 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.

30 mg (0.02 mmol, 5 mol%) ofpalladiumtetrakis(triphenylphosphine) are added to a solution of 200 mg (0.53 mmol, 1.0 eq.) of methyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]octanamide and 204 mg (0.80 mmol, 1.5 eq.) of ethyl 4-bromocinnamate in 3 ml of a mixture of dimethylformamide and of a 2M potassium phosphate solution (6/1). The reaction mixture is stirred at 80C for 2 hours. The reaction is halted by the addition of 5 ml of water and then extraction is carried out with ethyl acetate. The organic phases are combined and dried over sodium sulphate. The solvents are evaporated and then the residue is chromatographed on silica gel (heptane/ethyl acetate 80/20). 145 mg of ethyl 3-(3′-[((methyl)(octanoyl)amino)methyl]biphenyl-4-yl}acrylate are obtained in the form of an oil. Yield = 63%

The synthetic route of 24393-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2006/18325; (2006); A1;,
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Reference of 13078-21-2, The chemical industry reduces the impact on the environment during synthesis 13078-21-2, name is Ethyl 2-(2-methoxyphenoxy)acetate, I believe this compound will play a more active role in future production and life.

General procedure: A solution of corresponding substituted ethylaryloxyacetate (3a-f, 25 mmol) in ethanol (100 mL) was treated with 10% aqueous sodium hydroxide (9 mmol). After 4 h at room temperature and evaporation under reduced pressure of ethanol, the aqueous phases were acidified at pH 4 with HCl (2 N). Removal of precipitate by filtration yielded the crude acids, which were recrystallized in ethanol to afford substituted aryloxyacetic acid 4a-f, yield 66-90%.

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-(2-methoxyphenoxy)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhong, Yan; Xu, Yi; Zhang, Ai-Xia; Li, Xiao-Feng; Xu, Zhao-Ying; Li, Ping; Wu, Bin; Bioorganic and Medicinal Chemistry Letters; vol. 26; 10; (2016); p. 2526 – 2530;,
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Related Products of 19063-56-0, The chemical industry reduces the impact on the environment during synthesis 19063-56-0, name is 7-Bromo-2H-chromen-2-one, I believe this compound will play a more active role in future production and life.

General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel).

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, 7-Bromo-2H-chromen-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sipos, Zoltan; Konya, Krisztina; Synlett; vol. 29; 18; (2018); p. 2412 – 2416;,
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Synthetic Route of 29006-01-7, 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. 29006-01-7 name is Methyl 4-methoxybutanoate, 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 4-methoxybutyrate 1a (1.6 g, 12.1 mmol) was added to 50 mL of tetrahydrofuran, and the temperature was lowered to -78 C.using a dry ice-acetone bath. Lithium bis-trimethylsilylamide (12.7mL) was addedslowly. 12.7 mmol). After completion of the addition, the reaction was stirred for 1 hour.Trimethylchlorosilane (1.31 g, 12.1 mmol) was added. The reaction was continued for 20 minutes with the addition of N-bromosuccinimide(2.15 g, 12.1 mmol). ), The reaction was stirred for 2 hours.The dry ice-acetone bath was removed, the temperature of the reaction solution was naturally raised to room temperature, thereaction was quenchedwith saturatedammonium chloride solution, the reaction solution was extracted with ethyl acetate (50 mL×3), the organic phases were combined, and the organic phases were separately used with water(50 mL). It was washed with sodium chloride solution (50 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure.The resulting residue was purifiedby silica gel column chromatographyusing eluent system B to give the title product 1b (900 mg, colorless oil).

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

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; Yang Fanglong; Chi Jiangtao; He Feng; Tao Weikang; (33 pag.)CN107793396; (2018); A;,
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Reference of 7778-83-8, 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 7778-83-8 as follows.

General procedure: To a deoxygenated solution of ethyl cinnamate (176 mg, 1 mmol)and NaN3 (98 mg, 1.5 mmol) in anhydrous MeCN, a deoxygenatedsolution of CAN (1.370 g, 2.5 mmol) in the same solvent (10 mL)was added dropwise at 0 C and stirred well. H2O (400 mL) wasadded to the reaction mixture and the aqueous layer was extractedwith CH2Cl2 (4 × 150 mL). The combined organic extracts werewashed with H2O (2 × 100 mL), and dried over anhydrous Na2SO4.The crude residue, on treatment with anhydrous NaOAc (123 mg,1.5 mmol) in anhydrous acetone (5 mL), followed by usual workupand purification by silica gel column chromatography using petroleumether-EtOAc (98:2) as eluent, afforded 2a as a pale yellowviscous liquid.

According to the analysis of related databases, 7778-83-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hu, Manman; He, Xinwei; Niu, Zhiqiang; Yan, Zhenglei; Zhou, Fuyin; Shang, Yongjia; Synthesis; vol. 46; 4; (2014); p. 510 – 514;,
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