Category: 5905-69-1

Related Products of 5905-69-1, 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 5905-69-1 as follows.

A. 2-(4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolaneA mixture of commercially available l-bromo-4-(difluoromethoxy)benzene (1 g, 4.48 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.2g, 4.71 mmol), potassium acetate (1.3 g, 13.4 mmol), and PdCl2(dppf)-CH2Cl2 Adduct (0.18 g, 0.22 mmol) in DMF (15 mL) was stirred under nitrogen at 90 0C for 1 hour. Diluted with DCM, washed with water, sat. NaHCC^, brine, dried (MgSC^), and concentrated.The crude was purified using ISCO flash chromatography (silica gel/ hexanes/ethyl acetate 100:0 to 50:50 gradient) to afford the desired product 2-(4- (difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane 13A (1.12 g, 3.32 mmol, 74.0 % yield) as a brown oil.

According to the analysis of related databases, 5905-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; AHMAD, Saleem; WASHBURN, William, N.; HERNANDEZ, Andres, S.; ROBL, Jeffrey, A.; NGU, Khehyong; WANG, Zhenghua; WO2010/104830; (2010); 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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-4-(difluoromethoxy)benzene

Example 178 2-[5-[4-(Difluoromethoxy)phenyl]-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-methyl-N-phenylacetamide To a solution of the compound synthesised in Reference Example 36 (50.0 mg, 122 mumol), 1-bromo-4-(difluoromethoxy)benzene (20.1 muL, 147 mumol) and tetrakistriphenylphosphine palladium (7.08 mg, 6.12 mumol) in 1,4-dioxane (2.0 mL) is added a solution of potassium carbonate (50.8 mg, 367 mumol) in water (0.40 mL), and the mixture is stirred under reflux for 2 hours. After the reaction, the reaction mixture is poured into water at 0C, and extracted with ethyl acetate. The organic layer is washed with a saturated saline solution, and dried over anhydrous sodium sulfate. The drying agent is removed by filtration, and the solvent is evaporated under reduced pressure. The obtained crude product is purified by silica gel chromatography (hexane/ethyl acetate = 3/1) to give 2-[5-[4-(difluoromethoxy)phenyl]-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-methyl-N-phenylacetamide (21.1 mg, 41 %). IR (cm-1): 696, 1111, 1495, 1674, 1774

The synthetic route of 5905-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1719761; (2006); 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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, A new synthetic method of this compound is introduced below., Product Details of 5905-69-1

Step 4) 1-difluoromethoxy-4-{3-[3-(2-fluoro-ethyl)-cyclobutyl]phenyl-ethynyl}benzene {3-[3-(2-Fluoro-ethyl)-cyclobutyl]-phenylethynyl}-triisopropyl-silane (349 mg, 0.973 mmol) was dissolved in THF (2 ml) and treated with a 1M solution of tetrabutylammonium fluoride (TBAF) in THF (2 ml) at room temperature. The crude product obtained from aqueous work-up was placed in a CEM snap top microwave vial and combined with 1-Bromo-4-Difluoromethoxybenzene (300 mg 1.30 mmol), copper iodide (35 mg, 0.131 mmol), tetrakis(triphenylphosphine)palladium (70 mg, 0.060 mmol) and triethylamine (4.3 g, 42.5 mmol). The vial was quickly agitated then irradiated in a CEM Explorer microwave instrument for 30 minutes at 80 C. Purification by column chromatography (gradient; 0%, then 5% EtOAc in hexanes) afforded an oil 178 mg (53%). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.68-1.80 (m, 2H) 1.85-2.11 (m, 2H) 2.17-2.36 (m, 2H) 2.38-2.43 (m, 1H) 3.28-3.65 (m, 1H) 4.24-4.52 (m, 2H) 7.01-7.47 (m, 5H) 7.18 (d, J=8.8 Hz, 2H) 7.58 (d, J=8.8 Hz, 2H).

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; WYETH; US2009/48320; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

5905-69-1, 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.

(Reference Example 71) Ethyl 1-[4-(difluoromethoxy)phenyl]piperidine-4-carboxylate[0521] Sodium tert-butoxide (2.29 g, 23.8 mmol), palladium(II) acetate (428 mg, 1.91 mmol), and tri-tert-butylphosphine (370 muL, 1.52 mmol) were added to a solution of ethyl piperidine-4-carboxylate (3.52 mL, 22.9 mmol) and 1-bromo-4-(difluoromethoxy)benzene (4.25 g, 19.1 mmol) in toluene (122 mL), and the mixture was stirred at 80C for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate = 100/0 – 90/10] to obtain the title compound (3.17 g, yield: 56%). [0523] 1H-NMR (400 MHz, CDCl3) delta: 7.07-7.00 (2H, m), 6.95-6.87 (2H, m), 6.41 (1H, t, J = 75 Hz), 4.16 (2H, q, J = 7 Hz), 3.61-3.55 (2H, m), 2.84-2.73 (2H, m), 2.47-2.39 (1H, m), 2.08-1.99 (2H, m), 1.95-1.83 (2H, m), 1.27 (3H, t, J = 7 Hz).

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; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; OHKAWA, Nobuyuki; TAKANO, Daisuke; KUBOTA, Hideki; ONODA, Toshio; KANEKO, Toshio; ARAI, Masami; TERASAKA, Naoki; EP2862861; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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

Piperidine-4-carboxylic acid ethyl (3.52mL, 22.9mmol), and 1-Bromo-4- (difluoromethoxy) benzene (4.25g, 19.1mmol) of TorrEne (122 mL) to the solution, sodium tert- butoxide (2.29g, 23.8mmol), palladium acetate (II) (428mg, 1.91mmol), and, tri -tert- butyl phosphine (370muL, 1.52mmol) was added, and 30 minutes at 80 And the mixture was stirred. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, the resulting organic layer was washed with saturated brineAfter, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Siri resulting residue wasGel column chromatography [elution solvent: hexane / ethyl acetate = 100 / 0-90Purification by / 10], the title compound (3.17 g, yield: 56%) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5905-69-1, its application will become more common.

Reference:
Patent; Daiichi Sankyo company limited; Sato, Rie; Kobayashi, Katsuhiro; Kaneko, Toshio; (188 pag.)JP2015/113323; (2015); A;,
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

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