Author: Jessica.F

Electric Literature of 651734-58-6,Some common heterocyclic compound, 651734-58-6, name is Methyl 2-fluoro-3,5-dimethoxybenzoate, molecular formula is C10H11FO4, 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.

b. methyl 2-chloro-6-fluoro-3,5-dimethoxybenzoate S02C12 (2.20g, 0.016mol) was added dropwise to a solution of methyI-2-fluoro-3,5-dimethoxy benzoate (3.5g, 0.016 mol) in acetonitrile (40mL) at 0C under nitrogen atmosphere. The resulting reaction mixture was warmed to room temperature slowly and stirred for lh. The reaction mixture was quenched with saturated sodium bicarbonate solution, and extracted with ethyl acetate (3x30mL). The organic phase was washed with brine, dried over Na2S0 , filtered, and concentrated. The residue was purified by silica gel column chromatography using eluent (gradient hexane/ether (20:1) to hexane/ether (5:1) to afford the title compound (2.7g, yield: 67%) as a solid.

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-fluoro-3,5-dimethoxybenzoate, its application will become more common.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; REYNOLDS, Dominic; HAO, Ming-Hong; WANG, John; PRAJAPATI, Sudeep; SATOH, Takashi; SELVARAJ, Anand; WO2015/57938; (2015); 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. 73792-12-8, name is Ethyl 4-amino-3-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 73792-12-8

Step 1 : Ethyl 3-fluoro-4-hydrazinylbenzoate hydrochloride: To a stirred and cooled (-20C) solution of ethyl 4-amino-3-fluorobenzoate (18 g, 98.809 mmol) in cone. HC1 (200 mL) was added aqueous solution of NaN02 (7.5 g, 108.69 mmol). This mixture was added very slowly to a precooled (-10 C) mixture of and tin chloride (100 g, 444.7 mmol) in cone. HC1 (80 mL) and stirred at the same temperature for 30 min. The precipitate obtained was filtered and washed with diethyl ether (2 x 100 mL) to obtain 19.6 g of the title compound as white solid. 1H NMR (300 MHz, DMSO-i) delta 1.30 (t, J = 7.2 Hz, 3H), 4.27 (q, J = 6.9 Hz, 2H), 7.19 (t, J = 8.1 Hz, 1H), 7.67 (d, J = 8.1 Hz, 1H), 7.78 (d, J = 8.4 Hz, 1H), 8.94 (br s, 1H), 10.50 (br s, 2H); APCI-MS (m/z) 199 (M+H)+.

According to the analysis of related databases, 73792-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; DAS, Sanjib; CHAUDHARI, Sachin Sundarlal; THOMAS, Abraham; PARDESHI, Shailesh Ramesh; DESHMUKH, Vishal Govindrao; WADEKAR, Prashant Dilip; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; WO2015/87234; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1312610-07-3, name is Ethyl 7-bromobenzo[d][1,3]dioxole-4-carboxylate, 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 1312610-07-3, Formula: C10H9BrO4

To a solution of compound I-IXa (700 mg, 2.6 mmol) in toluene (15.0 mL), EtOH (3.0 mL)Aq. Na2CO3 (2.0 M, 1.5 mL) and 4-(methoxycarbonyl)phenylboronic acid,The mixture was stirred under a nitrogen atmosphere for 10 minutes, then Pd(Ph3P)4 (90 mg, 0.08 mmol) was added and the flask was purged three times with nitrogen.The mixture was stirred at 80 C for 10 hours.After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and washed with water and brine.Solvent removal and purification of the residue on silica gel by column chromatography(eluent: PE: EtOAc = 6:1)Compound I-IXb (560 mg, yield 59%) was obtained as a yellow 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, Ethyl 7-bromobenzo[d][1,3]dioxole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Beijing Kaiyin Technology Co., Ltd.; Xiong Guoyu; Yang Jian; Zhou Desheng; Pan Hai; Yan Fukun; (19 pag.)CN108675998; (2018); A;,
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Some common heterocyclic compound, 18014-00-1, name is Dimethyl 2,5-dibromoterephthalate, molecular formula is C10H8Br2O4, 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 C10H8Br2O4

Raw material 1 (11.6 g, 55 mmol) and methyl 2,5-dibromoterephthalate (17.6 g, 50 mmol) were dissolved in 200In ml of toluene, add 50 ml of 2M aqueous sodium carbonate and 50 ml of ethanol.After purging with nitrogen for 30 minutes, catalyst tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 3.5 g, 3.0 mmol) was added and heated to 100C with stirring.After 15 hours of reaction, cooling at room temperature, adding dichloromethane and deionized water, extracting the organic phase and drying over anhydrous magnesium sulfate,After filtration, depressurizing, concentrating, and separation and purification with a silica gel column, about 21.6 g (41 mmol) of pure Intermediate 1 was obtained in a yield of about 82%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18014-00-1, its application will become more common.

Reference:
Patent; Shanghai Hehui Optoelectric Co., Ltd.; Wang Liping; (15 pag.)CN107573357; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 94-46-2, name is Isoamyl Benzoate, 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 94-46-2, Safety of Isoamyl Benzoate

Trifluoromethylthio silver (0.5 mmol), 2,6-lutidine (0.1 mmol) and ammonium persulfate (1.0 mmol) were added to the reaction flask, and after evacuating the argon three times, isoamyl benzoate 1.0 mmol) and acetonitrile (5 mL). The reaction flask was placed in an oil bath at 90 C start heating and stirring 2h removed, to be cooled to room temperature. Using trifluoromethylbenzene as an internal standard substance, it was confirmed by 19F-NMR that 3-methyl-3-trifluoromethylthiobutyl benzoate was formed (a yield of 63%). The reaction mixture was filtered and the filtrate was evaporated to remove the solvent by a rotary evaporator. The residue was separated by column chromatography and concentrated under reduced pressure to give a colorless oil (75 mg, yield 51%).

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; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Chen Qingyun; Liu Chao; Wu Hao; Xiao Zhiwei; (15 pag.)CN104557358; (2017); B;,
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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. 53088-68-9, name is Methyl (3-Chlorophenyl)acetate, A new synthetic method of this compound is introduced below., Formula: C9H9ClO2

REFERENCE EXAMPLE 30 Methyl (RS)-a-bromo-(3-chlorophenyl)acetate A mixture of Reference Example 29 (5.0 g), N-bromosuccinimide (5.3 g) and azobisisobutyronitrile (0.38 g) in dry chloroform (50 ml) was heated at reflux for 6 hours. The reaction mixture was washed four times with water (50 ml) and the organic phase dried over magnesium sulphate and evaporated. The residual oil was purified by flash chromatography on silica eluding with a mixture of ethyl acetate and pentane (5:95, v/v). Fractions homogenous in the required product were combined and evaporated to give the title compound (4.3 g) as an oil.

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; Rhone-Poulenc Rorer Limited; US6048893; (2000); A;; ; Patent; Rhone-Poulenc Rorer Limited; US6124343; (2000); A;,
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Electric Literature of 69038-74-0, These common heterocyclic compound, 69038-74-0, name is tert-Butyl 3-Bromobenzoate, 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.

(+)-Pinanediol 3-(teri-butoxycarbonyl)benzeneboronate (12b). A solution of tert- butyl 3-bromo-benzoate (1.70 g, 6.61 mmol), obtained from 3-bromobenzoic acid, (Wright, S. W. et al, Tetrahedron Lett. 1997, 38, 7345-7348) and freshly distilled triisopropyl borate (1.53 mL, 6.61 mmol) in THF (17 mL) was cooled to -100 °C under argon flow and w-butyllithium (2.5 M soln in hexane, 2.91 mL, 7.27 mmol) was added dropwise over 15 min, during which the solution turned cherry red. After 1 h at -100 °C, trimethylsilyl chloride (0.84 mL, 6.61 mmol) was dropped into the reactor and the resulting colorless solution was allowed to warm to room temperature and stirred overnight. Finally, (+)-pinanediol (1.12 g, 6.61 mmol) was added and the solution stirred 1 h at room temperature. The mixture was partitioned between ethyl acetate (100 mL) and water (40 mL) and the aqueous phase was extracted with ethyl acetate (2 x 50 mL). The combined organic phases were washed with brine, dried over MgS04, filtered and concentrated in vacuo. The crude residue was purified by column chromatography (light petroleum/ethyl ether 95:5), affording 12b as a yellowish solid (2.10 g, 89percent yield). Mp 70-71 °C. [CC]D +7.3 (c 1.1, CHCI3). XH-NMR (400 MHz, CDC13): delta 0.94 (3H, s, pinanyl CH»), 1.24 (1H, d, J 10.9, pinanyl Hendo), 1.36 (3H, s, pinanyl G¾), 1.53 (3H, s, pinanyl CH3), 1.64 (9H, s, f-Bu), 1.98-2.30 (5H, m, pinanyl protons), 4.51 (1H, dd, J 8.5, 2.0, CHOB), 7.46 (1Eta, t, J7.6, ¾), 8.0 (1Eta, d, J 7.6, H4), 8.12 (1H, d, J7.6, H6), 8.45 (1H, s, H2). 13C-NMR (100 MHz, CDCI3): delta 24.0, 26.5, 27.1, 28.2, 28.7, 35.5, 38.2, 39.5, 51.4, 78.4, 80.9, 86.5, 127.6, 131.5, 132.1, 135.7, 138.7, 169.5, CB not seen. EI-MS: m/z 356 (M+, 10percent), 300 (36), 283 (41), 231 (50), 204 (38), 83 (65), 67 (59), 57 (100). Anal. Calcd. for C2iH29B04: C, 70.80; H, 8.20. Found: C, 70.55; H, 8.22.

The synthetic route of 69038-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; UNIVERSITA’ DEGLI STUDI DI MODENA E REGGIO EMILIA; SHOICHET, Brian K.; PRATI, Fabio; CASELLI, Emilia; ROMAGNOLI, Chiara; EIDAM, Oliv; WO2013/56163; (2013); A1;,
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Synthetic Route of 3195-24-2, These common heterocyclic compound, 3195-24-2, name is Diethyl 2,2-diallylmalonate, 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.

General procedure: In a 10 mL tube, the supported catalyst (0.002 mmol Ru) was dried for 1 h under vacuum (1.0 mbar). Then a solution of diene (0.1 mmol) in dry and degassed solvent (1 mL) was transferred via a cannula to the tube containing the catalyst under argon. The resulting suspension was stirred at the target temperature and the conversion was monitored by GC until the end of the experiment. At this time, the stirring was stopped, the material was left to settle and the solution was filtered via a cannula under nitrogen. The recovered catalyst was washed with dry and degassed solvent (3×3 mL), dried under vacuum and directly used in the next cycle. The filtrates were concentrated under reduced pressure to afford the corresponding RCM product, whose yield was determined by 1H NMR spectroscopy.

The synthetic route of 3195-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Monge-Marcet, Amalia; Pleixats, Roser; Cattoen, Xavier; Wong Chi Man, Michel; Tetrahedron; vol. 69; 1; (2013); p. 341 – 348;,
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Synthetic Route of 87661-20-9, 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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 72 (2S)-1-({1-[2-(3-Chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-cyclopropylamino}-acetyl)-pyrrolidine-2-carbonitrile The title compound was prepared in analogy to example 60 starting from 4-chloromethyl-5-methyl-2-(3-chloro-phenyl)-oxazole and tert.butyl cyclopropanecarboxylate. The starting material could be prepared from 3-methylbenzaldehyde and 2,3-butanedione oxime as described for benzaldehyde in Chem. Pharm. Bull. 1971, 19, 2050-2057. Steps A] and C] were performed as outlined in example 60, step B] was done according to example 69. The title compound was obtained as a brown gum. MS (ISP): 399.3 (MH+) and 401.3 (MH+).

The synthetic route of tert-Butyl cyclopropanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer, Markus; Hunziker, Daniel; Kuehne, Holger; Loeffler, Bernd M.; Sarabu, Ramakanth; Wessel, Hans P.; US2003/130281; (2003); 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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C8H14O2

To a solution of 1M LDA (42.1 mmol, 42.1 mL) at – 78 C was added dropwise t-butylcyclopropane carboxylate (5.0 g, 35.1 mmol) in 70 mL THF. After 1.5 hours, a solution of allyl bromide (3.03 mL, 35.1 mmol) in 10 mL THF was added. The reaction mixture was allowed to warm slowly to room temperature. After 18 hours, the reaction was quenched with saturated NH4CI (aq), and partitioned between EtOAc and H2O. The organic and aqueous layers were separated, and the aqueous layer was washed with 2 c 20 mL ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified on an 80 g silacel column, eluting with 0-15% EtOAc/hexanes. The product fractions were concentrated in vacuo to yield 1-allyl-cyclopropanecarboxylic acid tert-butyl ester, 2.48 g (38% yield). 1H NMR (CHLOROFORM-d) d: 5.73-6.01 (m, 1H), 4.91-5.13 (m, 2H), 2.27 (dt, J=6.6, 1.3 Hz, 2H), 1.42 (s, 9H), 0.99-1.20 (m, 2H), 0.49-0.73 (m, 2H).

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; BIOHAVEN PHARMACEUTICAL HOLDING COMPANY LTD.; CONWAY, Charles M.; DUBOWCHIK, Gene M.; PELLETIER, Jeffery Claude; REITZ, Allen B.; (186 pag.)WO2020/77038; (2020); A1;,
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