Tag: M.W=200-300

Application of 697762-67-7, 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. 697762-67-7, name is Methyl 5-bromo-2-chloro-3-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 20 methyl 5-bromo-2-chloro-3-methoxybenzoate (25.0 g, 89.4 mmol) in 13 THF (100 mL), 21 H2O (100 mL) and MeOH (100 mL) was added aq. 5 N 26 NaOH solution dropwise at 0 C. The mixture was stirred at room temperature for 1 hour. 24 conc. HCl was added to the mixture to acidify and the mixture was extracted with EtOAc (500 mL×2). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to afford the 27 title compound (22.6 g, 96%) as an orange solid. 1H NMR (400 MHz, CDCl3) delta 7.55 (s, 1H), 7.13 (s, 1H), 3.89 (s, 3H); [M+H]+ 265.

The synthetic route of Methyl 5-bromo-2-chloro-3-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAEWOONG PHARMACEUTICAL CO., LTD.; GREEN CROSS CORPORATION; YOON, Hee-kyoon; PARK, Se-Hwan; YOON, Ji-Sung; CHOI, Soongyu; SEO, Hee Jeong; PARK, Eun-Jung; KONG, Younggyu; SONG, Kwang-Seop; KIM, Min Ju; PARK, So Ok; (55 pag.)US2019/169174; (2019); 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. 116419-94-4, name is Methyl 4-methyl-3-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 4-methyl-3-(trifluoromethyl)benzoate

To a solution of 4-methyl-3-trifluoromethylbenzoic acid (1.71 g, 8.37 mmol) in DMF (20 mE) was added potassium carbonate (1.39 g, 10.1 mmol) and the reaction mixture was stirred at room temperature for five minutes. lodomethane (0.78 mE, 12.5 mmol) was added and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine (x2). The organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated at reduced pressure to afford methyl 4-methyl-3-trifluo- romethylbenzoate. The material was dissolved in carbon tetrachloride (10 mE) and treated sequentially with N-bromosuccinimide (2.74 g, 15.4 mmol) and benzoyl peroxide (catalytic) and heated at 80 C. for 18 hours. The mixture allowed to cool and diluted with water. The mixture was poured through a hydrophobic fit and the solvent evaporated at reduced pressure to afford methyl 4-(dibromom- ethyl)-3-trifluoromethylbenzoate. The material was dissolved in acetone/water (25 mE/S mE) and silver nitrate (2.38 g, 14.0 mmol) added. The reaction mixture was stirred at room temperature for 72 hours. The suspension was filtered through a pad of celite and the filtrate diluted with ethyl acetate. The solution was washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was dissolved acetone/ water (25 mE/S mE) and silver nitrate (2.38 g, 14.0 mmol) added. The reaction mixture was stirred at room temperature for 24 hours. The suspension was filtered through a pad of celite and the filtrate diluted with ethyl acetate. The solution was washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (eluent-100% i-hexane to 8:1 i-hexane/ethyl acetate) to afford the title compound (0.537 g, 33%). 1H NMR (400 MHz, CDC13); oe 10.46-10.45 (m,1H), 8.46 (s, 1H), 8.35 (d, J=8.2 Hz, 1H), 8.20 (d, J=8.2 Hz,1H), 4.00 (s, 3H).

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; CHIESI FARMACEUTICI S.p.A.; RANCATI, Fabio; RIZZI, Andrea; CARZANIGA, Laura; LINNEY, Ian; KNIGHT, Chris; SCHMIDT, Wolfgang; (176 pag.)US2016/235734; (2016); A1;,
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Reference of 29263-94-3,Some common heterocyclic compound, 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, molecular formula is C8H13BrO4, 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 7 mL vial equipped with magnetic stir bar was added bromomalonate (1.0 equiv,0.40 mmol), 2,6-lutidine (1.0 equiv, 0.40 mmol), tris[2-phenylpyridinato-C2,N]iridium(III) (1 mol %, 4.0 mumol), and heterocycle (5.0 equiv, 2.0 mmol). Dryacetonitrile or DMA (0.5 mL, 0.8 M) was then added and the reaction was sparged withN2 for 15 min. The reaction was set to stir under nitrogen at room temperature surroundedby a string of 1W or two strings of 4W blue LEDs for 24 h. The reaction mixture wasthen diluted with ethyl acetate and extracted with water. The aqueous layer was extractedwith ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine,dried over Na2SO4, and concentrated in vacuo. The residue was purified bychromatography on silica gel, using the solvent system indicated.

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

Reference:
Article; Swift, Elizabeth C.; Williams, Theresa M.; Stephenson, Corey R. J.; Synlett; vol. 27; 5; (2016); p. 754 – 758;,
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Reference of 55666-43-8, These common heterocyclic compound, 55666-43-8, name is tert-Butyl 3-bromopropanoate, 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.

0.3 g of the molecule 5 was dissolved in 5 ml of dry DMF,Cold to 0 degrees,Adding 40 mg of sodium hydride,Reaction for 15 minutes,Adding one equivalent of t-butyl 3-bromopropionate,Reaction for half an hour, warming up to 50 degrees reaction 24 hours,Rotate DMF, add 20 ml of water,Ethyl acetate extraction, combined organic phase,Saturated with salt water, anhydrous sodium sulfate drying, pumping, spin drying, and then silica gel column to get the molecular 6, the yield of 45%

Statistics shows that tert-Butyl 3-bromopropanoate is playing an increasingly important role. we look forward to future research findings about 55666-43-8.

Reference:
Patent; University of Science and Technology of China; Zhang Guoqing; Chen Biao; Xu Cheng; Wang Hao; Du Jiajun; Bi Guoqiang; Luo Yi; (111 pag.)CN107118586; (2017); A;,
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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. 3044-06-2, name is Diethyl 2-(1-ethoxyethylidene)malonate, A new synthetic method of this compound is introduced below., name: Diethyl 2-(1-ethoxyethylidene)malonate

4-isopropoxy-3-cyanobenzidine hydrochloride (1 g, 0.0042 mol), M-230 (1.06 g, 0.0046 mol),A fresh methanol solution of sodium ethoxide (3 g of sodium hydride (20%) was added to 100 ml of ethanol at a low temperature) (20 ml), and refluxed for 2 hours. After the reaction was completed by TLC, the reaction mixture was cooled to room temperature, and 6N was gradually added to the reaction mixture. ofThe pH of the mixture was adjusted to 1 with HCl, stirred for 30 min, filtered, filtered, washed with water and dried. The obtained crude product was recrystallized from ethanol to give a white solid, 0.44 g.Yield: 31.1%

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; Shenyang Hainuowei Pharmaceutical Technology Co., Ltd.; Wang Shaojie; Mao Qing; Zhang Bing; (30 pag.)CN110156698; (2019); A;,
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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. 57381-43-8, name is Methyl 2,5-dibromobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6Br2O2

General procedure: Method A:16,17 A two-necked round-bottomed flask equipped with a reflux condenser and a magnetic stir bar was charged with the 2-bromobenzoic acid (20mmol) and freshly distilled methanol (25mL). The solution was heated in a hot water bath, conc. H2SO4 (8mmol) was added slowly and the reaction mixture was refluxed for 24h. After cooling to room temperature around half of the amount of the solvent was removed in vacuo and the residue was partitioned between water (50mL) and diethyl ether (70mL). The organic layer was separated and washed with saturated NaHCO3 (2×50mL), water (50mL) and brine (50mL), dried over anhydrous MgSO4 and the volatiles were removed under reduced pressure. The crude product thus obtained was purified by flash chromatography on silica gel to afford the alkyl-2-halobenzoate. (0023) In a two-necked round-bottomed flask equipped with a reflux condenser and a magnetic stir bar the alkyl 2-halobenzoate (22.5mmol) was dissolved in freshly distilled dry THF (30mL) under argon. The solution was cooled to 0°C using an ice bath and NaH (60percent in mineral oil, 15mmol) was added portionwise. After stirring for 15min a solution of the alkyl acetate (15mmol) in dry THF (30mL) was added dropwise to the reaction mixture at 0°C. The mixture was warmed up, stirred at room temperature for 2h and heated under reflux for 24h. After cooling to room temperature around half of the amount of the solvent was removed in vacuo and the reaction mixture was diluted with toluene (50mL). The resulting mixture was washed with 2N HCl (50mL), saturated NH4Cl (50mL), dried over anhydrous MgSO4 and the volatiles were removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford the alkyl 3-(2?-halophenyl)-3-oxo-propanoate 1.

The synthetic route of 57381-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Weischedel, Heike; Sudheendran, Kavitha; Mikhael, Alevtina; Conrad, Juergen; Frey, Wolfgang; Beifuss, Uwe; Tetrahedron; vol. 72; 24; (2016); p. 3454 – 3467;,
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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 120974-97-2 as follows. name: (E)-Methyl 2-(methoxyimino)-2-(o-tolyl)acetate

1.5 1 of 25% strength ammonia water are added to 120 g (0.5 mol) of methyl E-2-methoximino-2-(2-methylphenyl)-acetate in 1.5 l of methanol and the mixture is refluxed for 5 hours. The reaction mixture is then allowed to cool, concentrated to approximately 1l, stirred with water and extracted by shaking with ethyl acetate. The organic phase is washed with water, dried over sodium sulphate and concentrated in vacuo. The residue is stirred with diisopropyl ether, filtered off with suction and dried. 66.2 g (69% of theory) of E-2-methoximino-2-(2-methylphenyl)-acetamide of melting point 98-99 C. are obtained.

According to the analysis of related databases, 120974-97-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Aktiengesellschaft; US6194464; (2001); B1;,
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Synthetic Route of 14062-25-0, These common heterocyclic compound, 14062-25-0, name is Ethyl 2-(4-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.

2.0 M LDA in heptane/THF/ethylbenzene (6.0 mL, 12 mmol) was slowly added to a solution of ethyl (4-bromophenyl)acetate (2.43 g, 10.0 mmol) in THF (20 mL) at -78 C. and then the mixture was stirred for 30 min. Methyl iodide (0.93 mL, 15 mmol) was added at -78 C. and then the reaction was stirred for an additional 30 min. Saturated NH4Cl aq. was added to quench the reaction. The mixture was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (0-10%) to afford the desired product (2.0 g).

The synthetic route of 14062-25-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YAO, Wenqing; ZHANG, Colin; XU, Meizhong; ZHUO, Jincong; HE, Chunhong; US2012/165305; (2012); 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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1000342-11-9

[01042] Step 5: methyl l-acetyl-6-bromo-lH-indazole-4-carboxylate[01043] To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (15 g, 61.5 mmol) in chloroform (150 mL), was added potassium acetate (6.32 g, 64.4 mmol) and acetic anhydride (12.6 g, 122.9 mmol) and reaction mixture was stirred at room temperature for 12 h. After this time, tert-butyl nitrite (25.3g, 246.1 mmol) and 18-crown-6 (5.7 g, 21.5 mmol) were added and reaction stirred again at 65 C for 3 h. On completion, the reaction mass was cooled to room temperature, diluted with chloroform (500 mL) and washed with sat. sodium bicarbonate solution. The organic layer was dried over sodium sulfate and concentrated to afford the title compound (18 g, 98.3%).

According to the analysis of related databases, 1000342-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; CHESWORTH, Richard; DUNCAN, Kenneth, William; WO2012/118812; (2012); A2;,
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Related Products of 40876-98-0, These common heterocyclic compound, 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, 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.

[4-((1S,3R,5R)-(1R,6S,8S)-8-bicyclo[4.3.1]dec-8-yl-8-aza-bicyclo[3.2.1]oct-3-yl)-3-oxo-3,4-dihydro-quinoxalin-2-yl]-acetic acid ethyl ester (d2) To a solution of c6 (578 mg, 1.64 mmol) in ethanol (6 mL) was added oxalacetic acid diethyl ester sodium salt (977 mg, 4.41 mmol) and acetic acid (0.505 mL, 8.83 mmol) at temperature of about 25 C. under a nitrogen atmosphere. The mixture was stirred at 100 C. for 8 hr. The reaction mixture was diluted with saturated aqueous NaHCO3, then extracted with CHCl3 (2*30 mL). The combined organic phases were washed with saturated aqueous NaCl and dried (MgSO4) and concentrated. The resulting brown solid was chromatographed (silica-gel 45 g, AcOEt/n-hexane=1/3?1/0) to provide 385 mg of compound d2 as a light brown solid. (Yield 49%) d2: 1H-NMR (300 MHz, CDCl3-CD3OD-DCl) delta: 1.18-1.46 (m, 10H), 1.60-1.94 (m, 7H), 2.14-2.58 (m, 8H), 2.82-3.10 (m, 2H), 3.19 (d, J=16.5 Hz, 0.5H), 3.50 (d, J=16.5 Hz, 0.5H), 4.06-4.38 (m, 6H), 5.80-6.26 (m, 1H), 6.93-8.18 (m, 4H); LC/MS: m/z=478.4 [M+H]+ (Calc: 477).

The synthetic route of 40876-98-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; Purdue Pharma L.P.; MARRA, Jeffrey Michael; Tsuno, Naoki; Ueno, Tatsuhiko; Zhou, Xiaoming; US2014/187544; (2014); A1;,
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