Tag: M.W=200-300

These common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, 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. 5905-69-1

A stirred mixture of l-bromo-4-(difluoromethoxy)benzene (0.54 mL, 4 mmol), bis(pinacolato)diboron (1.21 g, 4.8 mmol), l, -bis(diphenylphosphino)ferrocene- palladium dichloride (0.32 g, 0.4 mmol), and potassium acetate (1.18 g, 12 mmol) in dry 1,4-dioxane (10.0 mL) was purged three times with argon and placed under vacuum three times. The mixture was heated to 90 C and monitored with LC- MS and TLC. After 21 h, the reactions were cooled to rt then filtered through celite. The organic solvent was removed under reduced pressure, and the residue was purified on silica gel (0-10% EtOAc in hexanes) to yield a yellow liquid as 2- (4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l ,3,2-dioxaborolane. 1H NMR (400 MHz, DMSO-de) delta ppm 7.76 (2 H, m), 7.30 (3 H, m), 1.29 (12 H, s).N-(5-(4-(Difluoromethoxy)phenyl)-2-morpholinopyridin-4-yl)-5,7-difluoro-3- methyl-2-(pyridin-2-yl)quinolin-4-amine.

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 5905-69-1.

Reference:
Patent; AMGEN INC.; DRANSFIELD, Paul, John; GONZALEZ LOPEZ DE TURISO, Felix; KOHN, Todd, J.; PATTAROPONG, Vatee; SIMARD, Jillian, L.; WO2012/3283; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, 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. 5905-69-1

A stirred mixture of l-bromo-4-(difluoromethoxy)benzene (0.54 mL, 4 mmol), bis(pinacolato)diboron (1.21 g, 4.8 mmol), l, -bis(diphenylphosphino)ferrocene- palladium dichloride (0.32 g, 0.4 mmol), and potassium acetate (1.18 g, 12 mmol) in dry 1,4-dioxane (10.0 mL) was purged three times with argon and placed under vacuum three times. The mixture was heated to 90 C and monitored with LC- MS and TLC. After 21 h, the reactions were cooled to rt then filtered through celite. The organic solvent was removed under reduced pressure, and the residue was purified on silica gel (0-10% EtOAc in hexanes) to yield a yellow liquid as 2- (4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l ,3,2-dioxaborolane. 1H NMR (400 MHz, DMSO-de) delta ppm 7.76 (2 H, m), 7.30 (3 H, m), 1.29 (12 H, s).N-(5-(4-(Difluoromethoxy)phenyl)-2-morpholinopyridin-4-yl)-5,7-difluoro-3- methyl-2-(pyridin-2-yl)quinolin-4-amine.

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 5905-69-1.

Reference:
Patent; AMGEN INC.; DRANSFIELD, Paul, John; GONZALEZ LOPEZ DE TURISO, Felix; KOHN, Todd, J.; PATTAROPONG, Vatee; SIMARD, Jillian, L.; WO2012/3283; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

458-50-4, A common compound: 458-50-4, name is 4-Bromo-3-fluoroanisole, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: To a solution of 2-bromo-4-fluorobenzonitrile (0.30 g, 1.5 mmol) and cyclopropanol (0.14 g, 2.4 mmol) in DMF (4 mL) wasadded Cs2CO3 (0.88 g, 2.7 mmol) in a 25 mL single-necked round-bottom flask. After that, themixture was stirred at 25 ¡ãC under nitrogen. After stirring for 4 h, the resulting mixture was dilutedwith H2O (30 mL) and extracted with MTBE (10 mL¡Á3). Then the combined organic phase waswashed with saturated aqueous NaCl (10 mL¡Á3) and dried over Na2SO4 for 0.5 h. After that, theorganic phase was filtered under reduced pressure and the filtrate was concentrated underreduced pressure to give product as a yellow sticky substance. Then a mixture of 30 mL MTBE and100 mL n-hexane was added to dissolve the yellow sticky substance. Subsequently, the solutionwas cooled for 30 minutes with the mixture of water and ethanol. Lastly, the solution was filteredunder reduced pressure and the filtrate was dried naturally to obtain desired product in 80.3percentyield (0.29g).

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, 4-Bromo-3-fluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jin, Hao; Gao, Zhuo; Zhou, Shaodong; Qian, Chao; Synlett; vol. 30; 8; (2019); p. 982 – 986;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

32338-02-6, 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. 32338-02-6 name is 2-Bromo-4-methoxyaniline, 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.

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 ¡ãC for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

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

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 103291-07-2, name is 4-Bromo-1-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 103291-07-2, 103291-07-2

4-Bromo-1-fluoro-2-methoxybenzene a15 (0.0204 g, 0.10 mmol), acridine photosensitizer (A) (0.0029 g, 0.005 mmol) and L-valine were added sequentially under argon atmosphere. Ethyl b1 (0.0218 g, 0.15 mmol), 1,2-dichloroethane (DCE) 2.0 mL.The reaction was irradiated under a 6W blue light lamp at 50 C for 72 h.After completion of the reaction, the solvent was evaporated under reduced pressure and purified by column chromatography, eluting solvent: (V) petroleum ether / (V) ethyl acetate = 30/1.Yellow liquid (32) (0.0109 g, 94%) was obtained.

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, 4-Bromo-1-fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (27 pag.)CN110294685; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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

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

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