Category: 262587-05-3

Electric Literature of 262587-05-3, These common heterocyclic compound, 262587-05-3, name is 1-Bromo-3-(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.

93 mg of 1 -bromo-3(dofluoromethoxy)benzene (0.42 mmol; 1.00 eq) and the successively 142 mg of 1 -[3-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]azetidine-3-carboxylic acid (preparation 9; 0.42 mmol; 1.00 eq) dissolved in 4 mE of DME, 3.4 mg of Pd(dppf)C12, CH2C12 (0.01 eq.) and finally 127 mg of CsF (0.83 nnol; 2.00 eq) were introduced into a microwave- resistant 10 mE reaction vessel. The reaction mixture was microwave-irradiated for 1 h at 120 C. The reaction medium was then taken up with ethyl acetate and water, while adjusting the pH to 6, and then extracted with ethyl acetate and washed with brine. The organic phase was dried over magnesium suflate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (l3iotage 10 g silica 15-40 jtmlliquid deposit in dichloromethane) using a cyclohexane/0% to 100% dichloromethane gradient. The fractions containing the targeted product were combined and then evaporated, under reduced, pressure to give 99 mg of title compound in the form of a colorless oil,Yld: 33%.10548] ?H NMR (300 MHz, CHC13-d) oeppm 2.24 (s, 3H)3.41-3.49 (m, 1H) 3.62 (s, 3H) 3.92-4.02 (m, 4H) 6.18 (s, 1H) 6.32 (s, 1H) 6.43 (t, J=74 Hz, 1H) 6.68 (s, 1H) 6.93-6.96 (m, 1H) 7.19-7.3 1 (m, 3H).EC-MS mlz (M+H): 348.

The synthetic route of 262587-05-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INVENTIVA; BOUBIA, Benaissa; MASSARDIER, Christine; GUILLIER, Fabrice; POUPARDIN, Olivia; TALLANDIER, Mireille; AMAUDRUT, Jerome; BONDOUX, Michel; FEENSTRA, Roelof Williem; VAN DONGEN, Maria Johana Petronella; (207 pag.)US2017/66717; (2017); A1;,
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Some common heterocyclic compound, 262587-05-3, name is 1-Bromo-3-(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. SDS of cas: 262587-05-3

General procedure: To a mixture of l-bromo-3-(difluoromethoxy) benzene (1 g, 4.5 mmol), bis(tri-tert- butylphosphine) palladium(O) (460 mg, 0.9 mmol) in 1,4-dioxane (30 ml) under argon atmosphere was added 0.5 M of 2-tert-butoxy-2-oxoethyl zinc chloride in ether (22.5 ml). The resulting mixture was stirred at room temperature overnight. The mixture was partitioned between saturated NH4C1 and EtOAc. The organic extract was washed with brine, dried over sodium sulfate, filtered and evaporated. The crude material was purified by silica gel chromatography eluting with 0-10% EtOAc in Hexane to afford 1119.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 262587-05-3, its application will become more common.

Reference:
Patent; CALITHERA BIOSCIENCES INC.; LI, Jim; CHEN, Lijing; GOYAL, Bindu; LAIDIG, Guy; STANTON, Timothy, Friend; SJOGREN, Eric, Brian; WO2013/78123; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 262587-05-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 262587-05-3, name is 1-Bromo-3-(difluoromethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a flask containing 1-bromo-3-(difluoromethoxy)benzene (350 mg, 1.58 mmol) and 1,4-dioxa-8-azaspiro[4.5]decane (249 mg, 1.74 mmol) in dioxane (10 mL) was added t-BuONa (303mg, 3.16 mmol), under N2 After being heated with stuffing at 100 C overnight, the resulting reaction mixture was cooled to rt, diluted with H20 (30 mL) and extracted with EA (30 mL) for three times. The combined organic layer was washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give 8-[3-(difluoromethoxy)phenyl]-1,4-dioxa-8-azaspiro[4.5]decane (450 mg), which was used in the next step without further purification.

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, 1-Bromo-3-(difluoromethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 262587-05-3, These common heterocyclic compound, 262587-05-3, name is 1-Bromo-3-(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.

EXAMPLE 1; Preparation of 2-nitro-5- (3-difluoromethoxyphenylthio) – p-xylene [nitroderivative of formula (III) ]; 4.36 g (0.109 moles) of sodium hydride are sus¬ pended in 80 ml of N, N-dimethylformamide at 0C. 20 g of 4-nitro-2 , 5-dimethylthiophenol (0.109 moles) dis¬ solved in 67 ml of N, N-dimethylformamide are added dropwise under stirring. 24.4 g of l-bromo-3- (difluoromethoxy) benzene (0.109 moles) dissolved in 20 ml of N, N-dimethylformamide are then added dropwise; catalytic Cu and CuCl are subsequently added and the reaction temperature is brought to 150 C for 1 h.After GC control, the reaction mixture is cooled to room temperature, filtered on a celite bed, diluted with water and extracted with ethyl acetate. The or¬ ganic phase is anhydrified with sodium sulfate, and then filtered and evaporated.The product thus obtained is purified on silica gel eluting with hexane/ethyl acetate 9:1. 30 g of the desired product are obtained. GC-MS : M+ = 325

Statistics shows that 1-Bromo-3-(difluoromethoxy)benzene is playing an increasingly important role. we look forward to future research findings about 262587-05-3.

Reference:
Patent; ISAGRO RICERCA S.R.L.; GUSMEROLI, Marilena; FILIPPINI, Lucio; PELLACINI, Franco; BRAVINI, Paolo; ELMINI, Alexia; VAZZOLA, Matteo Santino; BADARACCO, Christian; WO2012/25450; (2012); A1;,
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Ether | (C2H5)2O – PubChem

Reference of 262587-05-3, 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 262587-05-3 as follows.

A nitrogen-purged mixture of tris(dibenzylideneacetone)dipalladium(0) (0.0193 g, 0.021 mmol), and di-tert-butyl(2′,4′,6′-triisopropyl-3,4,5,6-tetramethyl-[1,1′-biphenyl]-2-yl)phosphine (0.0251 g, 0.052 mmol) in toluene (2.2 mL) was stirred for 20 minutes and then added to an nitrogen-purged mixture of methyl 3-cyclobutyl-4-[4-(morpholin-4-yl)piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-6-carboxylate (0.1760 g, 0.441 mmol, E509), 1-bromo-3-(difluoromethoxy)benzene (0.1179 g, 0.529 mmol), and Cs2CO3 (0.2143 g, 0.658 mmol). The mixture was heated to 70 C overnight, diluted with water, extracted with DCM (3 x 8 mL), dried (Na2SO4), and concentrated. The residue was chromatographed on silica (30-60% EtOAc/DCM to 4% MeOH/DCM) and re-chromatographed (2.5-4% zPrOH/DCM) to give the titled compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.28 – 8.16 (m, 2H), 7.58 (t, J = 8.2 Hz, 1H), 7.51 – 7.03 (m, 3H), 3.95 (dq, J = 18.1, 9.8, 8.5 Hz, 1H), 3.88 (s, 3H), 3.63 – 3.48 (m, 6H), 2.91 (t, J = 11.9 Hz, 2H), 2.53 – 2.48 (m, 4H), 2.46 – 2.28 (m, 2H), 2.12 – 1.88 (m, 4H), 1.63 (td, J = 13.1, 12.6, 6.4 Hz, 2H).

According to the analysis of related databases, 262587-05-3, the application of this compound in the production field has become more and more popular.

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. 262587-05-3, name is 1-Bromo-3-(difluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

A mixture of commercially available 1-boc piperazine (500.1 mg, 2.685 mmol) and commercially available 3-difluoromethoxybromobenzene (598.8 mg, 2.685 mmol) in toluene (20 ml) is placed in a 50 ml three-necked round-bottomed flask made inert with argon, and then the ligand (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (56.850 mg, 91.2 mumol) and palladium(II)acetate (20.4 mg, 91.2 mumol) are added. The reaction mixture is stirred and brought to reflux for 16 hours. After returning to 20 C., the reaction mixture is diluted with water (20 ml) and then extracted with ethyl acetate (2*30 ml). The organic extracts are combined, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The compound obtained is purified by chromatography on silica gel (AIT cartridge, Ref. FC-25 Si-BP-SUP, 20-40 mum, eluent dichloromethane, flow rate 20 ml/min). The fractions containing the expected compound are combined and then evaporated under reduced pressure. The expected tert-butyl 4-(3-difluoromethoxyphenyl)piperazin-1-ylcarboxylate is isolated (253 mg), the characteristics of which are as follows: LC/MS analysis: tr=4.18 min, M+H+ 329.31

According to the analysis of related databases, 262587-05-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharma S.A.; US2005/14765; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem