Tag: M.W=200-300

Related Products of 57486-69-8,Some common heterocyclic compound, 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, molecular formula is C9H9BrO2, 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: [2-(4-Chloro-phenoxy)-phenyl]-acetic acid (IX) Methyl 2-bromophenylacetate (47.0 grams 216.3 mmol) and 4-chloro-phenol (27.8 grams, 215.8 mmol) were dissolved in dioxane (790 ml) while warming to 50 C. To the resulting solution were added, under stirring in an inert nitrogen atmosphere, cesium carbonate (141 grams, 432.2 mmol) and copper(l) chloride (18.56 g, 86.2 mmol). Finally, N,N-dimethylglycine (4.46 grams, 43.2 mmol) was added to the green suspension. The reaction mixture was heated at 110 C. (reflux temperature) for 4 days while stirring. The reaction mixture was filtered over dicalite, which was washed with dioxane (40 ml). The dioxane was removed in vacuo to leave a brownish oil. Ethyl acetate (100 ml) was added to the oil and the pH of the resulting mixture was adjusted to 1 by addition of 1 M HCl (300 ml). The organic phase was washed with saturated brine (300 ml), dried on magnesium sulphate and then concentrated under vacuum to yield 57.2 grams (206 mmol; 95 %) of 2-(4-chloro-phenoxy)-phenyl]-acetic acid methyl ester as a brown oil.

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-(2-bromophenyl)acetate, its application will become more common.

Reference:
Patent; Organon Ireland Ltd.; Pfizer Inc.; US2006/229352; (2006); A1;,
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Electric Literature of 1415920-00-1, 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. 1415920-00-1 name is Ethyl 4-amino-3,5-difluorobenzoate, 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.

To a solution of ethyl 4-amino-3,5-difluorobenzoate (i-27b) (1 g, 4.98 mmol), t-BuONO (3769 mg, 7.46 mmol) in20 mL CH3CN at room temperature was added CuBr2 (1.66 g, 7.46 mmol). The mixture wasstirred at room temperature for 1 hour, diluted with water (40 mL), and extracted with EtOAc(40 mL*2). The combined organic layers were washed with brine, dried over Na2SO4,filtered and concentrated. The residue was purified by column chromatography on silica gel(PE/EA = 100/1 to 20/1) to afford the title compound (0.9 g, 68 % yield). LCMS (ESI) calc?dfor C9H7BrF2O2 [M+H]: 265, found: 265.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-amino-3,5-difluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth, Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard, Thomas; ZHANG, Dongshan; WO2014/28589; (2014); A2;,
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Related Products of 117324-58-0, 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. 117324-58-0 name is Methyl 2-amino-5-(trifluoromethyl)benzoate, 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.

To a solution of compound 13a (0.92 g, 4.2 mmol) and Boc 2O (3.17 g, 14.7 mmol) in THF (15 mL) was added DMAP (256 mg, 2.1 mmol) at 26-32C. The reaction was stirred at 26-32C for 4 h. The reaction solution was concentrated in vacuum to give the crude residue, which was purified by column chromatography on silica gel (0-10%EtOAc in petroleum ether) to afford the desired product compound 13b (1.43 g, 81.2% yield) as an off-white solid. LCMS: Rt = 1.078 min in 5-95AB_220&254. lcm chromatography (MERCK RP-18e 25-2mm), MS (ESI) m/z= 442.1 [M+23] +. 1H NMR (400MHz, CDCl 3) delta 8.28 (d, J=1.6 Hz, 1H), 7.95 (dd, J=2.0, 8.4 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 3.93 (s, 3 H), 1.36 (s, 18 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-5-(trifluoromethyl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD; LI, Zhengtao; ZOU, Hao; ZHU, Wei; SHEN, Changmao; WANG, Rumin; LIU, Wengeng; CHEN, Xiang; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (307 pag.)WO2019/149164; (2019); A1;,
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Some common heterocyclic compound, 41727-48-4, name is Methyl 4-amino-3,5-dichlorobenzoate, molecular formula is C8H7Cl2NO2, 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: Methyl 4-amino-3,5-dichlorobenzoate

EXAMPLE 5 1-Acetyl-2-(4-carbomethoxy-2,6-dichlorophenylimino)imidazolidine Methyl-4-amino-3,5-dichlorobenzoate (16.8 g, 31 mmole), 1-acetyl-2-imidazolidone (4.3 g, 33.5 mmole) in phosphoryl chloride (44 ml) were stirred at 50 C. for 3 days. After cooling the phosphoryl chloride was evaporated to give an oily residue. Iced water was added to the residue which was then basified with aqueous sodium hydroxide. The mixture was extracted with methylene chloride which was then washed with water, dried (magnesium sulphate) and evaporated to give a creamy solid. This solid was recrystallized from toluene to give the title compound (7.7 g) mp 188-189 C. Analysis calculated for C13 H13 Cl2 N3 O3: Theory: C, 47.30; H, 3.97; N, 12.73. Found: C, 47.34; H, 3.88; N, 12.60.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41727-48-4, its application will become more common.

Reference:
Patent; Beecham Group p.l.c.; US4505926; (1985); 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. 583-02-8, name is Ethyl 4-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl 4-(trifluoromethyl)benzoate

General procedure: A mixture of substituted ethyl benzoate 2 (10 mmol) and hydrazinehydrate (20 mmol) in ethanol was stirred at room temperaturefor 3 h and then filtered. The crude product recrystallizedfrom absolute alcohol to give 3a-l, which were used directly forthe next step. Under this same condition, the intermediate compounds 8a-d were also prepared.

The synthetic route of 583-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; He, Haifeng; Wang, Wei; Zhou, Yuan; Xia, Qin; Ren, Yanliang; Feng, Jiangtao; Peng, Hao; He, Hongwu; Feng, Lingling; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1879 – 1888;,
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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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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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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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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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Synthetic Route of 144267-97-0, 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 144267-97-0 as follows.

5-Fluoro-6-[5-(benzyloxy)benzifnid zol-l-yl]-l,3-dihvdro-l-hydwxy-2,l- benzoxaborole Preparation of ethyl 2-bromo-5-fluoro-4-(4-methoxy-2-nitrophenylamino) benzoate[0242] To a solution of 4-methoxy-2-nitroaniline (6 g, 22.6 mmol, 1 eq) and ethyl 2-bromo-4,5-difluorobenzoate (3.8 g, 22.6 mmol, 1 eq) in dry DMF (225 mL) was added CS2CO3 (12.7 g, 33.9 mmol, 1.5 eq) under N2 protection. The mixture was heated to 100C for 4h. TLC analysis showed there was no starting material remained. The mixture was mixed with 300mL water. The mixture was extracted with EA (2 x 100 mL) and the organic layer separated was washed with 0.5N HCl, water, brine and dried over anhydrous Na2S04. The mixture was filtered and the filtrate was concentrated. The solid was purified by recrystallization with EA/PE to give 6 g of product (yield 65%).

According to the analysis of related databases, 144267-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; ZHANG, Yong-kang; ZHOU, Huchen; DING, Charles; PLATTNER, Jacob, J.; FREUND, Yvonne; WO2011/63293; (2011); A1;,
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