Month: August 2021

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. 1535-73-5, name is 3-Trifluoromethoxyaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Trifluoromethoxyaniline

General procedure: Compounds 2-amino-5-methoxy-4-substitutedbenzonitriles (4a?4d) (10.0mmol) in 10 N hydrochloric acid (30.0mL) were cooled to 0 °C and diazotized with sodium nitrite (0.71g) in water (10.0mL). The diazonium solution was neutralized with excess of sodium acetate trihydrate and stirred for 2 h at 0 °C with the corresponding substituted anilines (10.0 mmol). The solution was kept overnight at 4 °C, filtered, and washed with water. The crude products were then purified by recrystallization with ethyl acetate to obtain intermediate (5a?5z). Compounds (5a?5z) were boiled in 70percent ethanol (25.0 mL) for 1h, and then evaporated under reduced pressure to dryness. Acetic acid (10.0 mL) was added and the solution was refluxed for 2 h, cooled, poured into water (100mL), filtered and dried. The crude products thus obtained were recrystallized from ethanol to give the final compounds 7-alkoxyl-6-methoxy-4-substituted-1,2,3-benzotriazines (6a?6z).

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:
Article; Zhao, Xing-Wang; Liu, Dan; Luan, Sheng-Lin; Hu, Guo-Dong; Lv, Jin-Ling; Jing, Yong-Kui; Zhao, Lin-Xiang; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7807 – 7815;,
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Reference of 7025-06-1, These common heterocyclic compound, 7025-06-1, name is 1-Bromo-2-phenoxybenzene, 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.

37A. (1-(2-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate To a -78° C. solution of 1-bromo-2-phenoxybenzene (283 mg, 1.136 mmol) in anhydrous THF (5 mL) was added dropwise n-BuLi (545 muL of a 2.5 M solution in hexane, 1.363 mmol). The reaction was stirred at -78° C. for 0.5 h, after which a solution of 4-oxocyclohexane-1,1-diyl)bis(methylene)bis(4-methylbenzenesulfonate (1E; 530 mg, 1.14 mmol) in THF (4 mL) was added dropwise. The reaction mixture was slowly warmed to rt and stirred at rt for 2 h. Analytical HPLC showed the reaction was complete. Powdered NaOH (91 mg, 2.27 mmol) was added and the mixture was stirred under reflux for 18 h. The reaction was cooled to rt, diluted with water and extracted with EtOAc (2*). The organic layer was dried (MgSO4) and concentrated in vacuo. The crude oil purified by flash chromatography (SiO2) using a gradient from 0percent to 40percent EtOAc/hexane (15 min) to give the title compound (230 mg, 0.495 mmol, 44percent yield) as a white solid. LCMS [M+H]+=465.1; 1H NMR (CDCl3) delta: 7.85-7.77 (m, 2H), 7.76-7.69 (dd, J=7.9, 1.9 Hz, 1H), 7.41-7.30 (m, 4H), 7.20-7.14 (td, J=7.6, 1.9 Hz, 1H), 7.14-7.06 (m, 2H), 6.98-6.92 (dd, J=7.6, 1.5 Hz, 2H), 6.83-6.76 (dd, J=8.1, 1.4 Hz, 1H), 3.87 (s, 2H), 3.75 (s, 2H), 2.59-2.50 (ddd, J=13.5, 11.3, 4.1 Hz, 2H), 2.48 (s, 3H), 1.98-1.87 (m, 2H), 1.75-1.64 (td, J=11.3, 10.8, 2.7 Hz, 2H), 1.60-1.51 (m, 2H).

The synthetic route of 7025-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhang, Hao; Cheng, Peter T.W.; Chen, Sean; Tao, Shiwei; Wu, Shung C.; Negash, Lidet A.; US2014/275173; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 50868-73-0, 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. 50868-73-0 name is 2-Methoxy-6-methylaniline, 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.

b) Preparation of intermediate 4; 3.3 g of intermediate 3 (24.1 mmoles) were dissolved in acetic acid (15 ml). Iodine monochloride (5.87g, 36 mmoles) was added. The mixture was stirred at room temperature for 30 minutes and was evaporated. The residue was suspended in an aqueous solution of Na2CC>3 and was extracted with dichloromethane. After drying the dichloromethane extract on MgSCU, it was evaporated and the residue was purified on a silica gel column using dichloromethane as eluent. Yield : 0.758g (13%) of intermediate 4 (CI-MS : 264 [M+H]+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methoxy-6-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; ARTS, Frank, Xavier, Jozef, Herwig; WO2006/15985; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 767-91-9, The chemical industry reduces the impact on the environment during synthesis 767-91-9, name is 2′-Methoxyphenyl acetylene, I believe this compound will play a more active role in future production and life.

General procedure: 1a-1e (0.5mmol) and alkynyl reagent 2a-2o (0.60mmol), Pd(OAc)2 (0.025mmol, 0.0056g) and dppf (0.025mmol, 0.0138g), piperazine (1mmol, 0.0861g) in THF (2mL) was added to a 20mL silica tubes. The autoclave was closed, flushed three times with CO, pressurized with 50psi of CO, and heated at 50C for 24h. After the completion of the reaction, the reactor was cooled down to room temperature, the crude products were extracted with ethyl acetate and water, and the organic layer were purified by column chromatography on silica gel using dichloromethane or ethyl acetate/petroleum ether as eluent. All products 3aa-3ea were identified by comparing their spectral data with those of authentic samples.

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, 2′-Methoxyphenyl acetylene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Shan; Sun, Huaming; Zhuang, Mengyuan; Zheng, Shaohua; Jian, Yajun; Zhang, Weiqiang; Gao, Ziwei; Molecular catalysis; vol. 452; (2018); p. 264 – 270;,
Ether – Wikipedia,
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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. 701-56-4, name is 4-Methoxy-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Methoxy-N,N-dimethylaniline

General procedure: N,N-dimethylaniline (0.4 mmol, 1.0 equiv.) and diphenyliodonium salts (0.8 mmol, 2.0 equiv.) were added to a dried Schlenk tube. The tube was degassed with Nitrogen for three times. Then Toluene (3.0 mL) were added via a syringe, finally add 0.8 mL LiHMDS (0.8 mmol, 2.0 equiv.) 1 mol/L solution in THF under ice bath conditions. The mixture was stirred at 110 oC for 16 h, and then cooled down to room temperature. The crude products were directly purified using flash column chromatography on silica gel (petroleum ether/ethyl acetate 100:1 as eluants) to afford the desired product.

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:
Article; Zhang, Zhiang; Wu, Xunshen; Han, Jianwei; Wu, Wenjun; Wang, Limin; Tetrahedron Letters; vol. 59; 18; (2018); p. 1737 – 1741;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, belongs to ethers-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 7252-83-7, category: ethers-buliding-blocks

i. Preparation of compound 311. 1-(2-Amino-3-chloro-4-hydroxy-phenyl)-ethanone 310 (40 g, 215 mmol) was dissolved in DMF (360 ml). Cesium carbonate (140 g, 430 mmol) was added, followed by bromoacetaldehyde dimethyl acetal (54.5 g, 323 mmol). The mixture was then vigorously stirred at 65 C for 24 hours. Upon cooling to room temperature, EtOAc (1 L) and H20 (1 L) were added to the mixture. The organic layer was extracted with EtOAc (1 x 400 ml). The combined organic layer was washed with aqueous 3% LiCI solution (2 x 1 L), brine, dried (Na2S04) and concentrated in vacuo. The residue was purified by silica gel chromatography to give compound 311 as a white solid (39 g, 67%).

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; GILEAD SCIENCES, INC.; RAY, Adrian S.; WATKINS, William J.; LINK, John O.; OLDACH, David W.; DELANEY, IV, William E.; WO2013/40492; (2013); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 592-55-2, These common heterocyclic compound, 592-55-2, name is 1-Bromo-2-ethoxyethane, 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.

To a solution of methyl 3-hydroxy-2-methylbenzoate (0.83 g, 5.00 mmol) in DMF (10 ml) was added potassium carbonate (1.38 g, 10.0 mmol) and potassium iodide (0.83 g, 5.00 mmol) followed by 2- bromoethyl ethyl ether (0.7 ml, 6.00 mmol). The reaction mixture was heated at 100 C with stirring. After 30 minutes, more 2-bromoethyl ethyl ether (0.5 ml, 4.3 mmol) was added and the heating continued for another 45 minutes. After cooling to room temperature, the mixture was poured into water and extracted with EtOAc (x3). The combined organic extract was washed with brine, dried (Na2S04), filtered and concentrated. Dry column vacuum chromatography (heptane : EtOAc 95 : 5 – 90 : 10 – 80 : 20) afforded 0.85 g (71% yield) of methyl 3-(2-ethoxyethoxy)-2-methylbenzoate as a solid. 1H NMR (400 MHz, CDC13) d 7.38 (d, 1H), 7.14 (t, 1H), 6.96 (d, 1H), 4.09 (m, 2H), 3.85 (s, 3H), 3.78 (m, 2H), 3.59 (q, 2H), 2.42 (s, 3H), 1.21 (t, 3H). MS (ESI, positive mode) m/z 261.1 [M+Na]+.

Statistics shows that 1-Bromo-2-ethoxyethane is playing an increasingly important role. we look forward to future research findings about 592-55-2.

Reference:
Patent; BASF AS; SKJAeRET, Tore; FRASER, David Alan; STEINEGER, Hilde Hermansen; (179 pag.)WO2020/74964; (2020); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, belongs to ethers-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 450-88-4, category: ethers-buliding-blocks

4-Fluoro-2-methoxybenzenethiol To a suspension of 2-bromo-5-fluoroanisole (2.00 g, 9.755 mmol) and elemental sulphur (0.468 g, 14.632 mmol) in dry THF (50 mL) was slowly added tert-butyl lithium in pentane (1.7 M, 12.6 mL, 21.46 mmol) AT-78C. The resulting suspension was allowed to stir at-78C for 60 mins before being poured onto saturated ammonium chloride solution (80 mL) and product extracted with diethyl ether (100 mL). The organic phase was washed with aqueous hydrochloric acid (2 N, 40 mL), with the resulting organic phase being dried (MgSO4) and the solvent evaporated in vacuo to give a pale yellow oil. This was treated to a pad of silica gel, eluting with hexane: ethyl acetate [95: 5] to give a pale yellow oil (1.50 g, 68%). ON (300 MHz, CDC13) 7.20 (1H, dd, Ar), 6.65-6. 55 (2H, d, AR), 3.90 (3H, s, OCH3), 3.68 (1H, s, SH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-fluoro-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/43903; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 1663-61-2, name is (Triethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2?3 equiv) and absolute ethanol (2?3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 °C for 12?72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5percentether in pentane. The following compounds were prepared:

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 1663-61-2.

Reference:
Article; Gavin, Joshua T.; Annor-Gyamfi, Joel K.; Bunce, Richard A.; Molecules; vol. 23; 11; (2018);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, molecular formula is C8H9F2NO2, 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: C8H9F2NO2

To a stirred solution of 2,6-difluoro-3,5-dimethoxyaniline (9.03 g, 47.7 mmol), sodium triacetoxyborohydride (38.0 g, 180 mmol) in methylene chloride (60 mL) / trifluoroacetic acid (30 mL), 4,6-dichloronicotinaldehyde (8.00 g, 45.5 mmol) was added in small portions at room temperature. After 1 hour, the volatiles were removed in vacuo and saturated aqueous NaHCC (200 mL) was added. The resulting mixture was extracted with DCM (3 x 150 mL). The organic layers were combined, dried over Na2S04, and concentrated. The residue was purified on silica gel (eluting with 0 to 0-40% EtOAc in hexanes) to afford the desired product (15.0 g). LC-MS calculated for C14H13CI2F2N2O2 [M+H]+ m/z: 349.0; found 349.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 651734-54-2, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; LU, Liang; WU, Liangxing; QIAN, Ding-Quan; YAO, Wenqing; (102 pag.)WO2016/134314; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem