Month: July 2021

These common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-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. HPLC of Formula: C9H9BrO2

INTERMEDIATE 72-(3-BromophenyD-2-methylpropionic acid methyl esterA solution of Intermediate 6 (15.85 g, 69.2 mmol) in THF (50 mL) was added as a steady stream over about 5 minutes to a suspension of sodium hydride (60% dispersion in mineral oil, 8.32 g, 208 mmol) in THF (100 mL) under nitrogen in an ice-water bath whilst maintaining the internal temperature between 1O0C and 200C. After the addition was complete, the mixture was stirred at r.t. for 1 h. The mixture was cooled again in an ice-water bath, and a solution of methyl iodide (10.6 mL, 24.6 g, 173 mmol) in THF (100 mL) was added slowly so as to maintain the temperature of the reaction at <25C. After the addition was complete the mixture was stirred for a further 15 minutes with the ice- water bath, and then for 18 h. The mixture was poured slowly (over a period of about 2 minutes) onto a mixture of ice (approximately 100 g) and saturated ammonium chloride solution (100 mL). The resulting mixture was evaporated and extracted with DCM (2 x 50 mL). The combined organic phases were dried (MgSO4), the solvent removed in vacuo and purified by column chromatography (SiO2, 10-100% EtOAc in heptane) to give the title compound (17.3 g) as a pale straw-coloured oil. deltaH (CDCl3) 7.48 (t, IH), 7.38 (m, IH), 7.23-7.29 (m, IH), 7.19 (t, IH), 3.66 (s, 3H), 1.56 (s, 6H). The synthetic route of Methyl 2-(3-bromophenyl)acetate has been constantly updated, and we look forward to future research findings. Reference:
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
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Synthetic Route of 205448-64-2, The chemical industry reduces the impact on the environment during synthesis 205448-64-2, name is Methyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-methoxybenzoate, I believe this compound will play a more active role in future production and life.

5-((3-Methoxy-4-methoxycarbonylanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (10 g, 29.8 mmol) was suspended in DOWTHERM A, (trade mark of Fluka Chemie AG), (125 ml) and heated to 180-190 C. over 30 minutes.. The starting material dissolved at 100 C. and carbon dioxide came off at approximately 180 C. The heating was stopped after a further 30 minutes and the product precipitated out as the temperature dropped.. Upon reaching 40 C. ether was added and the mixture was stirred for 30 minutes.. The solid was collected by filtration, washed with ether and dried under vacuum to give 7-methoxy-6-methoxycarbonyl-1,4-dihydroquinolin-4-one (5.56 g, 80%). 11H NMR Spectrum: (DMSOd6) 3.80 (s, 3H); 3.85 (s, 3H); 5.95 (d, 1H); 7.00 (s, 1H); 7.85 (d, 1H); 8.40 (s, 1H); 11.6 (br s, 1H); MS-ESI: 234 [MH]+;

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 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.; US6809097; (2004); B1;,
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1195768-18-3, name is Methyl 3-amino-2-fluorobenzoate, 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. Quality Control of Methyl 3-amino-2-fluorobenzoate

A stirred solution of methyl 3-amino-2-fluorobenzoate (7.32 g, 43.3 mmol) in pyridine (20 ml, 247 mmol) under argon was cooled in an ice-bath and treated portion-wise with 3,3,3-trifluoro-1 -propanesulfonyl chloride (10.0 g, 50.9 mmol) over 1 hour. The viscous orange-yellow mixture was magnetically stirred at room temperature overnight. The reaction mixture was partitioned between DCM and 4 M HCI (500 mL) and the separated organic phase was washed with water and brine (100 mL), dried (MgSO^, filtered andevaporated to obtain title compound (1 .82 g) a light purple solid.

The synthetic route of 1195768-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADAMS, Jerry, Leroy; FAITG, Thomas; KASPAREC, Jiri; PENG, Xin; RALPH, Jeffrey; RHEAULT, Tara Renae; WATERSON, Alex Gregory; WO2011/59610; (2011); A1;,
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Synthetic Route of 99548-54-6, 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. 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a flask was added methyl 3-bromo-2-methylbenzoate (2 Ig, 91.7 mmol), potassium hexacyanoferrate (II) trihydrate (9.7g, 22.9 mmol), Na2Ctheta3 (9.7g, 91.7 mmol) and Pd(OAc)2 (102 mg) in N,N-dimethylacetamide (100 mL). The flask’s atmosphere was evacuated and replaced with nitrogen, and the reaction mixture heated at 1200C for 10 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (150 mL). The resultant slurry was filtered and washed thoroughly with ethyl acetate (2 x 50 mL). The combined filtrate was washed with brine and water, dried over Na2SO4 and evaporated under reduced pressure. The residue obtained after the concentration was purified using flash chromatography (ethyl acetate-hexanes (1:9) as the eluent) to provide methyl 3-cyano-2-methylbenzoate (11.2g, 70% yield). 1H NMR spectrum (in DMSO-d6): delta 8.03 (d, J= 8.1 Hz, IH); 7.98 (d, J= 7.9 Hz, IH); 7.49 (t, IH); 3.84 (s, 3H); 2.65 (s, 3H).

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

Reference:
Patent; INOTEK PHARMACEUTICALS CORPORATION; WO2008/106619; (2008); A2;,
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Related Products of 35450-37-4, A common heterocyclic compound, 35450-37-4, name is Methyl 3-bromo-4-methoxybenzoate, molecular formula is C9H9BrO3, 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.

A mixture of methyl 3-bromo-4-methoxybenzoate (0.90 g, 3.67 mmol), [4-(2-ethoxyethoxy)-2,6-dimethylphenyl]boronic acid (0.87 g, 3.67 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.13 g, 0.15 mmol), 2-(dicyclohexylphosphino)biphenyl (79 mg, 0.22 mmol), tripotassium phosphate (1.56 g, 7.34 mmol) and toluene (20 mL) was stirred under a nitrogen atmosphere at 90C for 18 hr. After cooling the reaction mixture, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1) to give the title compound (0.71 g, yield 54%) as a yellow oil. MS (ESI+): 359 (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; Takeda Pharmaceutical Company Limited; EP1726580; (2006); A1;,
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Synthetic Route of 79909-92-5, 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 79909-92-5 as follows.

4-Amino-2,6-dimethyl benzoic acid (200 mg, 1.1 mmol) and NOBF4 (196 mg, 1.7 mmol) were heated in 1,2-dichlorobenzene at 100 C for 30 min. The solution was cooled and diluted with MeOH and water. A few pellets (2-3) of KOH were added, and the solution was heated at reflux for 16 h. The solution was concentrated. The residue was partitioned between Et2O and 1 N NaOH. The aqueous layer was extracted with Et2O. The aqueous layer was cooled to 0 C and acidified with conc. HCl (pH = 1-2). The aqueous layer was extracted with CH2Cl2. The organic layers were dried (Na2SO4). Filtration and concentration gave 58 mg (31 %) of the acid as a tan solid.

According to the analysis of related databases, 79909-92-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; EP1175401; (2005); B1;,
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Adding a certain compound to certain chemical reactions, such as: 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, 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 41841-16-1, Formula: C9H9BrO2

Step 1: Preparation of methyl 2-(4-bromophenyl)propanoate Methyl 2-(4-bromophenyl)acetate (220 mg) prepared in Step 1 of Example 1 was dissolved in dimethylformamide (3 mL), NaH (53 mg) was added thereto, and the mixture was stirred for 30 mins at room temperature. Iodomethane (0.14 mL) was added to the mixture which was heated to 50 C., followed by stirring for 2 hrs. The reaction mixture was cooled down to room temperature, and water and ethyl acetate were added to form an organic and an aqueous layer. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure, and purified by Prep. TLC (n-Hex:EA=1:1) to obtain the title compound (200 mg). 1H NMR (300 MHz, DMSO-d6): delta 7.50 (d, 2H), 7.27 (d, 2H), 3.81 (q, 1H), 3.58 (s, 3H), 1.37 (d, 3H)

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-(4-bromophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HANMI PHARMACEUTICAL CO., LTD.; Park, Chul Hyun; Kim, Won Jeoung; Jung, Young Hee; Kim, Nam Du; Chang, Young Kil; Kim, Maeng Sup; US2014/163226; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, 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 4224-69-5, Computed Properties of C5H7BrO2

A 250 mL three-necked flask was evacuated with nitrogen to protect it, and the milled magnesium bars (2.06 g, 84.64 mmol) and THF (40 mL) were added in this order.Turn on stirring, heat to 45 ~ 55 C and add a piece of iodine under reflux to turn into a red-brown solution.The compound of formula 1 (9.2 g, 42.32 mmol) was dissolved in 26 mL of tetrahydrofuran,Then slowly add 20 drops to the reaction system,When the reaction system solution has a reddish brown color, it turns into a yellow emulsion until it turns into a white solution.As the reaction proceeds, the reaction system solution will become a clear and transparent liquid.After the addition, the reaction was performed for 0.5 h to obtain a compound of formula 2.; A 500 mL round-bottomed flask was evacuated with nitrogen, and the compound of formula 3 (5.00 g, 27.93 mmol),THF (80 mL), CuI (8.38 mmol, 1.60g) and LiCl (55.86 mmol, 2.37g),The reaction system was placed in an ice-water bath at 0 C.The compound of formula 2 obtained by the reaction was added dropwise to the reaction system. After the addition, the reaction was carried out for 0.5 h, and the reaction was moved to room temperature for 2 h.After the reaction was completed, an appropriate amount of water was added, followed by extraction with ethyl acetate (40 mL × 3) three times. The organic phases were combined, washed with saturated brine, and dried over anhydrous sodium sulfate.Suction filtration, the filtrate was concentrated under reduced pressure, the crude product was separated and purified by silica gel column (eluent: petroleum ether: ethyl acetate = 30: 1)The compound of formula 4 (5.39 g, yield 82%) was obtained as a colorless oily liquid.

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:
Patent; Shanxi Tumor Institute; Yang Xihua; Ou Wentao; (17 pag.)CN110776488; (2020); A;,
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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. 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H13BrO2

Under a nitrogen atmosphere, 4. 07 g of potassium ethoxide and 150 mL of purified tetrahydrofuran were added to a 250 mL three-necked flask equipped with a refluxing device and 8 g of ethyl 2-cyclopentyl-2-cyanoacetate was added. The reaction was stirred at room temperature (about 25 C). And then slowly added dropwise to a solution of ethyl 2-bromoisovalerate (9. 2 g) in 50 mL of tetrahydrofuran,And the mixture was heated under reflux for 8 hours. The solvent was then removed by evaporation to give a red viscous liquid and a mixture of white solids. Extracted with ether, washed with water, 5% sodium hydrogencarbonate, and then washed with water until the organic phase was neutral. The organic phase was dried over anhydrous magnesium sulphate for 12 h. Filtering, concentrating the solvent to obtain crude product, and then vacuum distillation, the unreacted raw materials and low boiling point of the material evaporated, 2-cyclopentyl-3-isopropyl-2-cyano-succinate 9. 5 g. The mass spectrum and infrared spectrum of the product were consistent with the structure of the target compound.

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 609-12-1.

Reference:
Patent; China Petroleum & Chemical Corporation; SINOPECBeijing Research InstituteofChemicalIndustry; XIE, LUNJIA; TIAN, YU; FENG, ZAIXING; ZHAO, SIYUAN; SUN, ZHUFANG; (18 pag.)CN104418770; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 17449-48-8, name is Dimethyl 5-fluoroisophthalate, 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 17449-48-8, Recommanded Product: 17449-48-8

General procedure: An aqueous 1 M NaOH solution (1.0 eq)was added to a solution of diester No.12a-b (1.0 eq) in MeOH (1 mL/0.1 mmol of the diester). Afterstirring at room temperature for 16 h, the solution was acidified with aqueous 5% KHSO4 solution topH 3, diluted with water (20 mL) and extracted with EtOAc (3 x 20 mL). Combined organic extractswere washed with brine (20 mL), dried over anhydrous Na2SO4 and evaporated under reducedpressure to afford monoester.

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, Dimethyl 5-fluoroisophthalate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zogota, Rimants; Kinena, Linda; Withers-Martinez, Chrislaine; Blackman, Michael J.; Bobrovs, Raitis; Pantelejevs, Teodors; Kanepe-Lapsa, Iveta; Ozola, Vita; Jaudzems, Kristaps; Suna, Edgars; Jirgensons, Aigars; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 344 – 352;,
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