Category: ethers-buliding-blocks

The chemical industry reduces the impact on the environment during synthesis 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, I believe this compound will play a more active role in future production and life. 3401-47-6

General procedure: Preparation of catalyst: 10mL flask was charged with a stirrer, Pd(OAc)2 (0.02mmol, 2mol%), ligand (Sym-Phos, PPh3, PhPCy2, S-Phos) (0.04mmol, 4mol%) and 1mL of THF. The flask was evacuated, backfilled with argon, and the reaction mixture was stirred for 10min at ambient temperature. Such prepared catalyst was used in the coupling reactions. Similarly were prepared catalysts based on PdCl2 complexes. Reaction setup. A round-bottom flask containing magnetic stir bar was charged with 15mL of 0.3% aqueous solution of SDS and base (3mmol). Then aryl halide (1mmol) dissolved in a minimum amount of THF, arylboronic acid or its derivative (1.5mmol) and the pre-catalyst (see above) were added. The flask was placed in to the oil bath (kept at 60C) and reaction mixture was stirred for next 16h. The product was filtered or extracted with methylene chloride or (3¡Á10mL), then combined organic layer was dried over MgSO4, filtered, solvent was evaporated and the product was isolated by column chromatography. Yields: 63-99%.

The chemical industry reduces the impact on the environment during synthesis 3401-47-6. I believe this compound will play a more active role in future production and life.

Reference:
Article; Demchuk, Oleg M.; Kap?on, Katarzyna; Mazur, Liliana; Strzelecka, Dorota; Pietrusiewicz, K. Micha?; Tetrahedron; vol. 72; 42; (2016); p. 6668 – 6677;,
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2752-17-2, Adding a certain compound to certain chemical reactions, such as: 2752-17-2, name is 2,2′-Oxydiethanamine, 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 2752-17-2.

DIPEA (0.144 mL, 0.823 mmol) was added to a mixture of 6 (100.0 mg, 0.165 mmol) and 2,2′-oxydiethanamine (14.6 mg, 0.082 mmol) in DMF (0.82 mL) at rt. The mixture was cooled to 0 C before dropwise addition of T3P (0.145 mL, 50 wt % in EtOAc, 0.247 mmol), then let to gradually warm to rt. At 4 hr, volatiles were evaporated, and the reaction quenched with water and MeOH. The mixture was basified with NH4OH, filtered, and purified by reverse-phase HPLC (25-50% ACN in water, 5 mM NH4OH modifier) to afford 33% yield of white 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, 2,2′-Oxydiethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ross, Audrey G.; Benton, Bret M.; Chin, Donovan; De Pascale, Gianfranco; Fuller, John; Leeds, Jennifer A.; Reck, Folkert; Richie, Daryl L.; Vo, Jason; LaMarche, Matthew J.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 17; (2015); p. 3468 – 3475;,
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1484-26-0, Name is 3-Benzyloxyaniline, 1484-26-0, belongs to ethers-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.

Example 18; Preparation of Intermediate Compound 18C; Step A – Synthesis of Compound 18B; Compound 18A (commercially available) (10.0 g, 50.25 mmol) was dissolved in water at room temperature and to resulting suspension K2CO3 ( 3.8 g, 27.64 mmol) was added. 3- Chloro propionylchloride (7.0 g, 55.28 mmol) was added dropwise for 30 minutes and stirred ffoorr 22 hhoouurrss aatt RRTT.. TThhee pprreecciippiittaattee wwaass f fiilltteerreedd aanndd wwaasshheedc with water, 1 N HCl, dried at 500C under vacuum overnight to give 7.2 g of the product 18B.

Statistics shows that 3-Benzyloxyaniline is playing an increasingly important role. we look forward to future research findings about 1484-26-0.

Reference:
Patent; SCHERING CORPORATION; WO2009/32125; (2009); A1;,
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Adding some certain compound to certain chemical reactions, such as: 19056-41-8, name is 3-Bromo-4-methoxyaniline, 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 19056-41-8. 19056-41-8

2-Amino-3′-methoxybenzophenone. In a flame-dried round bottom flask, anthranilic acid N-methoxyl-N-methylamide (8.00 g, 44.4 mmol) and m-bromoanisidine (8.31 g, 44.4 g) were dissolved in 250 mL of THF and the resulting solution was cooled to -78 C. With vigorous stirring, 2 equiv of nBuLi in hexanes (55.5 mL, 1.6 M, 88.8 mmol) was added dropwise by a syringe pump at 0.6 mL/min. After 20 min, 80 mL of 1 N hydrochloric acid was carefully added, the mixture was extracted with ethyl acetate (600 mL), and the ethyl acetate was washed with water (300 mL) and brine (300 mL), dried over sodium sulfate and concentrated in vacuo. Flash chromatography with 95:5 hexanes/ethyl acetate afforded 6.92 g (69% yield) of 2-amino-3′-methoxybenzophenone as a yellow oil.

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 3-Bromo-4-methoxyaniline.

Reference:
Patent; Board of Regents, The University of Texas System; The Regents of the University of California; US6100254; (2000); A;,
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Some common heterocyclic compound, 2930-05-4, name is 2-((Benzyloxy)methyl)oxirane, molecular formula is C10H12O2, 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. 2930-05-4

General procedure: In a 20 mL pressure tube (for volatile amines) was combined epoxide (1.0 mmol, 1.0 equiv) and amine (1.5 mmol, 1.5 equiv) 6.7 mL of reagent grade DMF. The reaction vessel fitted with a stirbar, sealed, and heated at 60C for 12 h after which the vessel was allowed to cool to ambient temperature (not necessary for reactions not ran in pressure vessels) before receiving deionized water (50 equiv) in one portion. The vessel was resealed and stirred at 60C for an additional 12 h. Solvent was removed on a rotary evaporator (22.5 mbar at 35C) and the crude residue loaded directly onto a silica gel column.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2930-05-4, its application will become more common.

Reference:
Article; Lizza, Joseph R.; Moura-Letts, Gustavo; Synthesis; vol. 49; 6; (2017); p. 1231 – 1242;,
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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 658-89-9 as follows. 658-89-9

To a solution of 4-trifluoromethoxy-benzene-1, 2-diamine 2 (4.5 g, 23.4 itimol) and triethylamine (5.0 g, 49.5 iranol) in methylene chloride (100 ml) was added dropwise a solution of diphosgene (2.4 g, 12.1 mmol) in methylene chloride (10 ml) at 0-5C. The resulting suspension was stirred for 1 h at rt and filtered. The collected white solid was washed with water and dried to give 3.85 g (75%), mp 260-2620C.

According to the analysis of related databases, 658-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES, LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2006/50148; (2006); A2;,
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Adding some certain compound to certain chemical reactions, such as: 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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 20469-65-2. 20469-65-2

As follows are specific steps of: adding 3,5-dimethoxy-bromobenzene (1.74 g, 8.0 mmol, 1.0 equivalent (hereinafter referred to as ?eq?)) and a catalyst PdCl(PPh)(281 mg, 0.4 mmol, 0.05 eq) into a 100 mL Schlenk reaction flask; performing a cycle of vacuumizing and filling nitrogen gas in the flask for three times; adding dried and redistilled 1,2-dichloroethane (20 ml), triethylamine (7 ml, 40 mmol, 5.0 eq) and pinacol borane (HBpin) (3.5 ml, 24.0 mmol, 3.0 eq) into the reaction flask by a syringe; heating the reaction system to 90 C. and performing a reflux reaction for 4 hours; cooling the reaction system down to room temperature, then pouring the reaction solution into 20 ml water to terminate the reaction; extracting aqueous phases with ethyl acetate for several times and combining organic phases; washing the organic phases with a saturated saline solution and water for one time, respectively; drying with anhydrous magnesium sulfate and spin-drying the solvent; recrystallizing an obtained product in n-hexane/ethyl acetate to obtain a 1.8 g white solid with the yield of 85%. H NMR (400 MHz, CDCl) delta (ppm) 7.03 (s, 2H, benzene), 6.90 (s, 1H, benzene), 3.84 (s, 6H, -OCH3), 1.33 (s, 12H, -CH3).

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-3,5-dimethoxybenzene.

Reference:
Patent; TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY OF THE CHINESE ACADEMY OF SCIENCES; Li, Yi; Hao, Qingshan; Chen, Jinping; Zeng, Yi; Yu, Tianjun; US2015/353468; (2015); A1;,
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701-07-5, name is 2-(2′-Bromophenoxy)propane, belongs to ethers-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. 701-07-5

N-{2-chloro-2′-[(l-methyIethyl)oxy]-4-biphenylyI}-2-[4~(ethylsuIfonyI)phenyl]acetamideA mixture of l-bromo-2-[(l-methylethyl)oxy]benzene (38 mg), N-[3-chloro-4-(4,4,5,5- tetramethyl-l}3,2-dioxaborolan-2-yl)phenyl]-2-[4-(ethylsulfonyl)phenyl]acetamide (intermediate 6b, 90 mg), PdCl2(dppf)-CH2Cl2 adduct (10 mg) and Cs2C03 (69.1 mg) in acetonitrile (1.5 mL) and water (0.5 mL) was sealed in a vessel and heated in die microwave at 100C for 30 mins. The reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by MDAP to afford N-{2-chloro-2′-[(l-methylethyl)oxy]-4-biphenylyl}-2-[4- (etliylsulfonyl)phenyl]acetamide (12 mg) as a yellow solid. ?-NuMuKappa (600 MHz, DMSO-c ) delta ppm 1.11 (m, 9H), 3.28 (q, J= 7.2 Hz, 2H), 3.83 (s, 2H), 4.51 (m, 1H), 6.96 (t, J= 7.8 Hz, 1H), 7.09 (m, 2H), 7.22 (d, J= 6.4 Hz, 1H), 7.33 (m, 1H), 7.48 (m, 1H), 7.63 (d, J= 7.8 Hz, 2H), 7.86 (d, J= 7.8 Hz, 2H), 10.49 (s, 1H); MS(ES+) m/z Ml (MH^>.

Statistics shows that 701-07-5 is playing an increasingly important role. we look forward to future research findings about 2-(2′-Bromophenoxy)propane.

Reference:
Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; MENG, Qinghua; CHENG, Yaobang; YANG, Ting; ZHANG, Guifeng; XIANG, Jianing; WU, Chengde; WO2013/29338; (2013); A1;,
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588-96-5, A common compound: 588-96-5, name is p-Bromophenetole, 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: The Teflon-lined sealed tube (20 mL) was charged with a 1,4-dioxane solution of sodium fluoroalkoxide RFONa [freshly prepared from fluoroalkanol RFOH (3.3(n + 1) mmol) and Na (3.0 (n + 1) mmol) in 1,4-dioxane (5 mL)], unactivated arylbromide ArBrn (3.0 mmol), CuBr (0.3n mmol) and DMF (3.0n mmol). The sealed tube was heated to 110 C and stirred for 6 h. After the completion of reaction, the concentration of the mixture in vacuo gave a residue, to which was added methyl tert-butyl ether (MTBE, 20 mL) and diluted hydrochloric acid (10 mL, 1.0 mol/L). The organic phase was separated, and the aqueous phase was extracted with MTBE (10 mL 9 3). The combined organic layer was dried over anhydrous MgSO4, andthen concentrated in vacuo to supply a crude product. Lastly, the purification of the crude product provided the desired product via column chromatography on silica gel (eluents: petroleum ether/ethyl acetate 20:1).

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, p-Bromophenetole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Ying; Li, Yu-Dao; Chen, Cheng; Zhao, Jian-Hong; Liu, Hong-Wei; Liao, Dao-Hua; Ji, Ya-Fei; Research on Chemical Intermediates; vol. 42; 3; (2016); p. 2525 – 2537;,
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60792-79-2, Name is 2,2′-Oxybis(ethylamine) dihydrochloride, 60792-79-2, belongs to ethers-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.

A suspension of 0.2 M 2,2′-oxydiethylamine dihydrochloride (0.247 gm, 1.35 mmole) and 0.4 M DIEA (0.47 ml, 2.7 mmole) in 4.5 DMF was added to 3-nitro-1,8-naphthalic anhydride (0.018 gm, 0.073 mmole) and heated at 150 C with microwave treatment under nitrogen for 5 minutes. The mixture was cooled, treated with 25 ml 1.3 M aqueous TFA, and concentrated to about 2 ml. The residue was diluted with dichloromethane, washed with sat. NaCl, dried over MgSO4, and concentrated under vacuum to give N- aminoethylethoxy-3-nitro-1,8 naphthalimide 7. MS m/z 330 (M + H)+.

Statistics shows that 2,2′-Oxybis(ethylamine) dihydrochloride is playing an increasingly important role. we look forward to future research findings about 60792-79-2.

Reference:
Patent; GENENTECH, INC.; WO2006/60533; (2006); A2;,
Ether – Wikipedia,
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