Category: ethers-buliding-blocks

4463-59-6, Adding some certain compound to certain chemical reactions, such as: 4463-59-6, name is 1-(2-Bromoethoxy)-2-methoxybenzene, 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 4463-59-6.

Compound II 0.2g (0.36mmol) dissolved in DMF were added K2CO3 0.1g (0.72mmol), a catalytic amount of TBAB and compound III-6 0.17g (0.72mmol), at 80 C overnight. After completion of the reaction, water was added to the potassium carbonate was dissolved, ethyl acetate (20mL ¡Á 3). The combined organic phases were washed with 1N NaOH ¡Á 2,1N HCl ¡Á 2, with saturated NaCl ¡Á 2, dried over anhydrous Na2SO4 dry. Filtration, column chromatography (petroleum ether: ethyl acetate = 2) to give a white solid IV-6 0.16g, yield: 66.7%.

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 4463-59-6.

Reference:
Patent; CHINA PHARMACEUTICAL UNIVERSITY; HUANG, WENLONG; QIAN, HAI; WANG, XUEKUN; LI, YING; YANG, BAOWEI; LI, ZHENG; (23 pag.)CN103739581; (2016); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

The chemical industry reduces the impact on the environment during synthesis 21702-84-1, name is 2,4-Dibromo-1-methoxybenzene, I believe this compound will play a more active role in future production and life. 21702-84-1

53.2 g of 2,4-dibromoanisole (B30), 40.4 g of 2-methyl-3-butyn-2-ol, 3.81 g of copper iodide, 150 g of triethylamine, 75 g of tetrahydrofuran, and 14.0 g of bis ( Triphenylphosphine) palladium (II) dichloride was mixed, and the temperature was raised to 60 C and stirred for 7 hours.After cooling to room temperature, filtration was performed, and the filtrate was concentrated under reduced pressure. The obtained oily substance was purified by column chromatography [silica gel (600 g), hexane: ethyl acetate = 2: 1] to obtain 50.9 g of diol. (B31).

The chemical industry reduces the impact on the environment during synthesis 21702-84-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Xin Yue Chemical Industry Co., Ltd.; International Business Ye Machine Corporation; Ju Chengyilang; Du Bianwu; Xin Jingtianhuijie; Chang Jingyangzi; Ze Cunangzhi; Di Yuanqin; Ya Lishanda¡¤aidehua¡¤hesi; Ge Leigeli¡¤buleita; Dan Nier¡¤baoluo¡¤sangdesi; Lu Di¡¤J¡¤woyitaiciji; (58 pag.)CN110627600; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1462-37-9, A common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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.

Step A: To a suspension of NaH (688 mg, 27.8 mmol) in THF (80 mL) was added diethyl malonate (7.45 g, 46.5 mmol) dropwise. Then ((2-bromoethoxy)methyl)benzene (5 g, 23.2 mmol) was added. The reaction was heated to 90 ¡ãC for 5 hours. After cooling to room temperature, the mixture was diluted with EtOAc (50 mL), washed with water (50 mL x 2), dried over anhydrous Na2S04 and concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with a gradient of 10percent – 30percent EtOAc/hexanes to to afford diethyl 2-(2-(benzyloxy)ethyl)malonate (6.6 g, 22.5 mmol, 81percent yield) as a colorless oil.

The synthetic route of 1462-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; YUK, Inn H.; PURKEY, Hans; O’BRIEN, Thomas; WO2015/142903; (2015); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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 95 mg (0.32 mMol) 6-(amino-pyrimidin-4-ylsulfanyl)-naphthalene-1 -carboxylic acid, 85 mg (0.48 mMol) 3-trifluoromethoxy-aniline, 446 mul (3.2 mMol) Et3N and 4 mg (0.03 mMol) DMAP in 3 ml DMF, 0.37 ml (0.63 mMol) propylphosphonic anhydride are added. After 3 h at rt, the reaction mixture is worked up as described for Ex. 58, yielding the title compound: m.p.: 197-199 ¡ãC; MS: [M+1]+= 457.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Trifluoromethoxyaniline, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/31265; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding some certain compound to certain chemical reactions, such as: 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, 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 64115-88-4. 64115-88-4

I. Preparation of the intermediatesa. Preparation of sulfonyl chloridesa.1 3-Bromo-4-trifluoromethoxy-benzenesulfonyl chloride2.0 g of 1-bromo-2-(trifluoro-methoxy)benzene (8.3 mmol) were dissolved in 30 ml of dichloromethane. At 0-5C, 1.06 g of chlorosulfonic acid (9.13 mmol), dis- solved in 3 ml of dichloromethane, were added dropwise. The reaction mixture was stirred for 30 min at room temperature. Additional 5.5 equivalents of chlorosulfonic in dichloromethane were added to drive the reaction to completion. Standard work-up was followed and silica gel chromatography with n-heptane- dichloromethane (6:4) as eluent gave 2.19 g of the title compound.1H-NMR (CDCI3, 400 MHz): delta [ppm] 8.3 (d, 1 H), 8.05 (dd, 1 H), 7.5 (dd, 1 H).

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 1-Bromo-2-(trifluoromethoxy)benzene.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2007/118899; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, 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. 366-99-4

General procedure: Different aniline (0.75 mmol) was dissolved in CH3CN (10 mL) in a 25-mL round-bottomed flask and cooled to 0¡ãC in an ice bath. To this stirred mixture was added t-BuONO (1.125 mmol) followed by TMSN3 (0.9 mmol) dropwise. The resulting solution was stirred at room temperature for 2 h. Compound 2 (0.5 mmol), CuI(0.1 mmol) and Et3N (0.6 mmol) were then added and the reaction was stirred at room temperature. The progress of the reaction was monitored by TLC. After the completion of reaction, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate as eluting solution to afford the target compounds 3 [25?29]. The data of 3a?3w are shown as follows. We selected one compound, 3d, as a representative compound and signal positions of carbon protons were assigned.

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 366-99-4.

Reference:
Article; Chen, Xiulei; Xiao, Youxin; Wang, Gaolei; Li, Zhong; Xu, Xiaoyong; Research on Chemical Intermediates; vol. 42; 6; (2016); p. 5495 – 5508;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 58-73-1, name is 2-(Benzhydryloxy)-N,N-dimethylethanamine, A new synthetic method of this compound is introduced below., 58-73-1

(2) Synthesis of indomethacin-diphenhydramine salt Indomethacin (358 mg, 1 mmol) and diphenhydramine (255 mg, 1 mmol) were stirred at 50 – 60C for 30 min to give an indomethacin-diphenhydramine salt as a yellow starch syrup-like viscous liquid. infrared absorption spectrum (liquid membrane): 1680 cm-1 (amidecarbonyl of indomethacin), 1595 cm-1 (COO-)

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; Medrx Co., Ltd.; EP2128123; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 702-24-9 as follows. 702-24-9

3-(5-Amino-2,4-difluorophenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one (2.4 g, 7.5 mmol) and 4-methoxy-N-methylbenzylamine (10 mL) were combined in a sealed vessel and heated to 200¡ã C. overnight. The volatiles were removed in vacuo and the residue was purified by column chromatography to give 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2,4-difluorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (3 g, 91percent yield), which was used in the next step without further purification.

According to the analysis of related databases, 702-24-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

458-50-4, 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. 458-50-4, name is 4-Bromo-3-fluoroanisole, This compound has unique chemical properties. The synthetic route is as follows.

Into the solution of l-bromo-2-fluoro-4-methoxybenzene (1000 g, 4.88 mol, 1.00 equiv) in tetrahydrofuran (10 L) was added drop wise LDA (2561 mL, 1.05 equiv) at -78 ¡ãC under nitrogen. The resulting solution was stirred for Ih at -70 ¡ãC. Then to the above solution, (Z)-N-[(tert-butoxy)carbonyI]imino(tert-butoxy)fomamide (1 122 g, 4.87 mol, 1.00 equiv.) was added. The resulting solution was stirred for 1 h at -78 ¡ãC, The reaction was then quenched by the addition of 200 mL of methanol. The resulting mixture was concentrated under vacuum and dissolved in EA (6L) , washed with water (2L) for two times and organic layers concentrated under vacuum. This resulted in 1400 g (66percent) of the title compound as a white solid.

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; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; MILLS, James Edward John; MUNCHHOF, Michael John; (301 pag.)WO2019/79540; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 19056-40-7 as follows. 19056-40-7

Example A5; a) Preparation of intermediate compound 7; A solution of methyl chloroglyoxalate (0.0593 mol) in CH2Cl2 (50 ml) was added por- tionwise to a mixture of 4-bromo-3-methoxybenzenamine (0.0494 mol) and Et3N (0.0741 mol) in CH2Cl2 (50 ml), stirred at 0 0C. The resultant reaction mixture was stirred for 24 hours at room temperature. A saturated aqueous NaHCO3 solution was added. The organic layer was separated, dried (Na2SO4), filtered and the solvent was evaporated. The residue was treated with diethyl ether, subsequently filtered off and dried. Yield: 12.8 g of intermediate compound 7 (91 percent).

According to the analysis of related databases, 19056-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/71646; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem