Month: January 2021

96999-01-8, name is Methyl 1-bromocyclopropanecarboxylate, 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. Computed Properties of C5H7BrO2

A mixture of 12j (2.40 g, 10 mmol), 3a-3b (15 mmol) andCs2CO3 (9.77 g, 30 mmol) in DMF (50 mL) was stirred at 90 C(for 3a) or 120 C (for 3b) in N2 atmosphere until the completion of reaction as indicated by TLC (typically within 12 h). Oncooling to room temperature, the reaction mixture was pouredinto ice-water (200 mL), and the mixture thus obtained wasextracted with CH2Cl2 (3 ¡Á 100 mL). The combined extractswere washed with 5% brine (5 ¡Á 100 mL), dried over anhydrous Na2SO4 and evaporated on a rotary evaporator to aord aresidue, which was purifed by column chromatography to yield21a-21b after trituration with EtOAc/n-hexane.6-Bromo-4-methylthioquinoline (21a). 1.07 g (42%). Whitesolid, m.p. 88-90 C. 1H NMR, delta 8.75 (d, J = 4.8 Hz, 1H),8.14 (d, J = 1.6 Hz, 1H), 7.94 (d, J = 8.8 Hz, 1H), 7.90 (dd,J = 2.0 Hz and 9.2 Hz, 1H), 7.40 (d, J = 4.8 Hz, 1H), 2.66(s, 3H). 13C NMR, delta 149.97, 146.97, 145.21, 132.71, 131.85,126.63, 124.88, 119.56, 116.27, 13.37. ESI-HR-MS, calcd. forC10H9BrNS ([M(79Br)+H]+) 253.9639, found 253.9641; calcd.for C10H9BrNS ([M(81Br)+H]+) 255.9619, found 255.9628.

The synthetic route of 96999-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Xiansheng; Wu, Jingwei; Liu, Yuqiang; Xie, Yafei; Liu, Changying; Wang, Jianwu; Zhao, Guilong; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 7; (2017); p. 799 – 811;,
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Application of 21597-54-6, The chemical industry reduces the impact on the environment during synthesis 21597-54-6, name is Methyl 3-amino-2-naphthoate, I believe this compound will play a more active role in future production and life.

40 g of compound A-1 (264 mmol) was added to a 500 ml three-necked flask, 16 g of formic acid and 160 ml of formamide were added, and the mixture was heated to 135 C for 5 h, and the reaction of the raw materials was completed by TLC; 200 ml of water was added, and the mixture was kept at 20 to 30 C for 1 h, and filtered. The filter cake was rinsed with water and recrystallized from ethanol to give 36.4 g of Compound A-2, yield 93.1%, purity 98.2%.

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 3-amino-2-naphthoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yantai Jiu Mu Chemicals Co., Ltd.; Song Sisi; Chen Muxin; Li Xiangyang; Kong Xiangxing; Cui Lisha; (32 pag.)CN108178750; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate, 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 57381-59-6, COA of Formula: C8H6BrFO2

Example 2bExample la (1748 mg, 77% content, 1 1 ,80 mmol) is added to sodium hydride (60% suspension in mineral oil, 472 mg, 1 1.80 mmol) in THF (5 mL). Stirring is continued at room temperature for 45 min. Methyl 5-bromo-2-fluorobenzoate (1 100 mg, 4.72 mmol) in THF (5 mL) is added and stirring is continued at room temperature overnight. Example la (65 mg, 75% content, 0.43 mmol) is added to sodium hydride (60% suspension in mineral oil, 17 mg, 0.43 mmol) in THF (1 mL) and the resulting mixture added to the reaction mixture and stirring is continued at room temperature overnight. The reaction mixture is diluted with DCM, washed with saturated NH4CI, dried and concentrated under reduced pressure giving a residue. Trimethylsilyldiazomethane in hexanes (2M, 2.153 mL, 4.3 mmol) is added dropwise to the residue in DCM (5 mL) and MeOH (2.5 mL) cooled to 0C. Stirring is continued for 120 min, then the reaction mixture is evaporated under reduced pressure to furnish the title compound (200 mg, 50%> content, 7%>).HPLC-MS (Method 2): Rt = 1.38 minMS (ESI pos): m/z = 327 (M+H)+

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; BERTANI, Barbara; FERRARA, Marco; LINGARD, Iain; MAZZAFERRO, Rocco; ROSENBROCK, Holger; WO2013/17657; (2013); A1;,
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Reference of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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.

Tert-butyl(chloro)diphenylsilane (18 ml, 68 mmol, CAS No 58479-61-1 ) was added drop wise to a mixture of ethyl 4-hydroxycyclohexanecarboxylate (9.4 ml, 57 mmol, CAS No 17159-80-7), 1H-imidazole (9.68 g, 142 mmol, CAS No 16681-56-4) and N,N-dimethylpyridin-4-amine (348 mg, 2.85 mmol, CAS No 1 122-58-3) in dimethylformamid (81 ml), and the mixture was stirred at room temperature for 24 h. For work-up, the mixture was poured into water, extracted with ethyl acetate (3x) and the combined organic phases were washed until pH=7 as reached. The organic phase was dried over sodium sulfate and was concentrated under reduced pressure. The residue was purified by flash chromatography (340 g Snap cartridge, hexane/ethyl acetate gradient, 5percent -> 30percent ethyl acetate) to give the title compound (21 g)

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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 110661-91-1, Safety of tert-Butyl 4-bromobutanoate

a) A mixture of 3-chloro-4-hydroxy-5-methyl-benzonitrile (1.15 g, 6.87 mmol) and Cs2CO3 (13.43 g, 41.2 mmol) in DMF (45 mL) is stirred at rt for 30 min before tert.-butyl 4-bromobutanoate (1.55 g, 6.95 mmol) is added. The orange suspension is stirred at 65 C. for 72 h. Another portion of tert.-butyl 4-bromobutanoate (1.55 g, 6.95 mmol) is added and stirring is continued at 65 C. for 24 h. The mixture is dilued with water (150 mL) and extracted three times with DCM (3*50 mL) and EA (3*50 mL). The org. extracts are combined, dried over MgSO4, filtered and concentrated. The crude product is purified by MPLC on silica gel eluting with heptane:EA:methanol to give tert-butyl 4-(2-chloro-4-cyano-6-methylphenoxy)butanoate (645 mg) as a colourless oil; LC-MS: tR=1.01 min, [M+H]+=no mass detectable; 1H NMR (D6-DMSO): delta 7.94 (d, J=1.7 Hz, 1H), 7.75 (d, J=1.3 Hz, 1H), 3.95 (t, J=6.3 Hz, 2H), 2.46 (t, J=7.2 Hz, 2H), 2.30 (s, 3H), 1.98 (quint, J=6.6 Hz, 2H), 1.41 (s, 9H).

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

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; Bolli, Martin; Lescop, Cyrille; Mathys, Boris; Morrison, Keith; Mueller, Claus; Nayler, Oliver; Steiner, Beat; US2013/303514; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 106614-28-2, name is Methyl 2,4-difluorobenzoate, 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 106614-28-2, SDS of cas: 106614-28-2

Intermediate 28: Methyl 2-fluoro-4-(piperazin-1-yl)-benzoate Dimethyl sulfoxide (1.0 ml) was added to 544 mg of piperazine to prepare a suspension, and 368 mg of methyl 2,4-difluorobenzoate was added to the suspension. The mixture was stirred at 80 C. for 1 hr and was then cooled to room temperature. The reaction solution was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (development system: methylene chloride-methanol-concentrated aqueous ammonia=900:100:1) to prepare 274 mg of the title compound. Physicochemical Properties of Intermediate 28

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; Meiji Seika Kaisha, Ltd.; US6451800; (2002); B1;,
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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. 369-25-5, name is Methyl 3,4-difluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 3,4-difluorobenzoate

General procedure: 1,2-Dihydro-indazol-3-one (500 mg; 3.73 mmol; 1.00 eq.), cesium carbonate (3.64 g; 11.2 mmol; 3.00 eq.) and methyl 3,4-difluorobenzoate (1.28 g; 7.46 mmol; 2.00 eq.) were stirred at 120 C in a round bottom flask for 3 hours. 1,2-Dichloro-3-nitrobenzene (1.43 g; 7.46 mmol; 2.00 eq.) was added and the reaction mixture was heated at 120 C for an additional 2 hours. The reaction mixture was cooled and diluted in ethyl acetate (50 mL). The organic layer was washed with a saturated solution of NH4Cl (20 mL), a saturated solution of Na2CO3(20 mL) and brine (20 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified using silica gel chromatography using heptane/ethyl acetate (5/5) as eluent. Methyl 4-(3-(2-chloro-6-nitrophenoxy)-1H-indazol-1-yl)-3-fluorobenzoate was isolated as a pale orange solid (1.00 g; 60.7%).1H NMR (DMSO-d6) delta: 3.90 (s, 3H), 7.43 – 7.36 (m, 1H), 7.50 (dd,J =8.7, 3.9 Hz, 1H), 7.68 – 7.57 (m, 3H), 7.99 – 7.90 (m, 3H), 8.11 (dd,J =8.2, 1.5 Hz, 1H), 8.20 (dd,J =8.3, 1.6 Hz, 1H)MS-ESIm/z442 [MH+].

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 369-25-5.

Reference:
Article; Ouvry, Gilles; Bouix-Peter, Claire; Ciesielski, Fabrice; Chantalat, Laurent; Christin, Olivier; Comino, Catherine; Duvert, Denis; Feret, Christophe; Harris, Craig S.; Lamy, Laurent; Luzy, Anne-Pascale; Musicki, Branislav; Orfila, Danielle; Pascau, Jonathan; Parnet, Veronique; Perrin, Agnes; Pierre, Romain; Polge, Gaelle; Raffin, Catherine; Rival, Yves; Taquet, Nathalie; Thoreau, Etienne; Hennequin, Laurent F.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5802 – 5808;,
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Synthetic Route of 19063-55-9, These common heterocyclic compound, 19063-55-9, name is 6-Bromochromen-2-one, 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.

It mainly includes the following steps: taking the coumarin derivative (500 mg, 2.2 mmol) after bromination at the 6 position,N,N-dimethylbenzene derivative (618 mg, 2.5 mmol) and K2CO3 (133 mg), which are introduced para-borate borate.The solution was dissolved in a toluene-ethanol mixed solution (3:1, 80 ml).After passing nitrogen gas for 30 min, 15 mg of tetrakistriphenylphosphine palladium catalyst was added to the solvent, and the mixture was heated to 80 C, 1000 r / min, and reacted for 8 hours.After the reaction, it was cooled to room temperature, washed with a large amount of water and extracted with dichloromethane.After removing excess solvent by a rotary evaporator, 100 mL of a dichloromethane solution was added to dissolve the solid, washed with 40 mL of distilled water, and separated.The remaining water was removed with anhydrous sodium sulfate, separated, and dried.The crude product was separated and purified on a 200-300 mesh silica gel column using dichloromethane-n-hexane (volume ratio 2:5) as eluent to afford yellow compound A as shown in Fig. 2.The coumarin-type organic nonlinear optical material compound A obtained by the above production method had a yield of 60%.

Statistics shows that 6-Bromochromen-2-one is playing an increasingly important role. we look forward to future research findings about 19063-55-9.

Reference:
Patent; Shantou University; Xu Liang; Zheng Yusen; Long Xueting; Zhang Wenying; Lu Fushen; (10 pag.)CN109776471; (2019); A;,
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Application of 773873-95-3,Some common heterocyclic compound, 773873-95-3, name is Methyl 2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate, molecular formula is C9H6F2O4, 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.

[00193] (2,2-Difluorobenzo[d] [l,3]dioxol-5-yl)methanolMethod A: Methyl 2,2-difluorobenzo[Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/21982; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 26218-04-2, name is 2-Ethylhexyl 4-aminobenzoate, 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 26218-04-2, Product Details of 26218-04-2

77.5 g of a 20 wt % aqueous solution of Na2CO3, 190.0 g of xylene and 68.5 g of 2-ethylhexyl 4-aminobenzoate are loaded into a 1 litre flask equipped with mechanical stirrer, thermometer, reflux condenser and dropping funnel. Keeping the mixture stirred at 65 C., a solution of 47.1 g of 4-nitrobenzoyl chloride is added to 47.0 g of xylene. The resulting mixture is then heated to reflux for 1 h. The organic phase is cooled, and the reaction product precipitates. The product is recovered by filtration, washing with xylene and drying at 110 C. under vacuum, to obtain 83 g of yellow powder corresponding to 2-ethylhexyl 4-(4-nitrobenzamido) benzoate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Ethylhexyl 4-aminobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; 3V Sigma S.P.A.; Maestri, Francesco; Berte’, Ferruccio; (8 pag.)US2018/30001; (2018); A1;,
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