Category: 29578-39-0

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. 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

To a solution of 1-bromo-3-fluoro-5-methoxybenzene (15 g,73.16 rnmol), tris(2-methylphenyl)phosphane (1.781 g, 5.85rnmol) and ethyl acrylate (11.90 mL, 109.74 mmcl) in TEA (135 mL) was added palladium(II) acetate (0.329 g, 1.46 nimnol) at room temperature under nitrogen atmosphere, and the mixturewas stirred at 90C for 2 days. The solvent was evaporated under reduced pressure, the residue was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried overmagnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give ethyl (E)-3-(3-fluoro-5- methoxyphenyl)acrylate (14.2 g, 63.3 mmcl, 87%) as a colorless oil.

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 of 29578-39-0,Some common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, molecular formula is C7H6BrFO, 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.

General procedure: A flask is charged with bromoaryl derivative (1 eq.), piperazine (4-6 eq.), BINAP (0.06-0.22 eq.), NaOtBu (1.4-2.5 eq.) and toluene. The reaction mixture is degassed with N2 and Pd2(dba)3 (0.03-0.11 eq.) is added. Reaction mixture is heated at 100-110C for 2h-20h. The reaction mixture is extracted with HCl 1N solution. The aqueous layer is basified with NaOH 2N solution and extracted with EtOAc or DCM. The combined organic layers are washed with water and brine, dried (over anhydrous Na2SO4 or MgSO4), filtered and concentrated in vacuo to afford the expected arylpiperazine used without further purification

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-fluoro-5-methoxybenzene, its application will become more common.

Reference:
Patent; GALAPAGOS NV; LES LABORATOIRES SERVIER; LABEGUERE, Frederic, Gilbert; HENG, Rama; DE CEUNINCK, Frederic, Andre; ALVEY, Luke, Jonathan; AMANTINI, David; BREBION, Franck, Laurent; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene; PEIXOTO, Christophe; POP-BOTEZ, Iuliana, Ecaterina; VARIN, Marie, Laurence, Claire; (180 pag.)WO2017/211666; (2017); A1;,
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Electric Literature of 29578-39-0, These common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, 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 2 3-Bromo-5-fluorophenol To a solution of 1-bromo-3-fluoro-5-methoxybenzene (3.0 g, 0.015 mol) in dry CH2Cl2 (80 mL) under an inert atmosphere and cooled to -30 C. was added 1 M BBr3 (4.27 mL, 0.045 mol) in 21 mL of CH2Cl2 dropwise while maintaining temperature at -30 C. The reaction was stirred for 3 h at 0-5 C. and then the reaction mixture was quenched with aqueous saturated NaHCO3. Water was added and the mixture was extracted with CH2CO2 three times. The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness to give the title compound (2.54 g, 91%).

The synthetic route of 29578-39-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FAY, Lorraine Kathleen; Johnson, Douglas S.; Kesten, Suzanne Ross; Lazerwith, Scott E.; Morris, Mark Anthony; Stiff, Cory Michael; Meyers, Marvin Jay; Wang, Lijuan Jane; US2008/261941; (2008); A1;,
Ether – Wikipedia,
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Synthetic Route of 29578-39-0,Some common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, molecular formula is C7H6BrFO, 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 a solution of 3-bromo-5-fluoroanisole (250 mg, 1.22 mmol, 1 equiv) in anhydrous THF was added granules of magnesium (32 mg, 1.28 mmol, 1.05 equiv) under nitrogen. The mixture was heated to 60 C for 2 h. After cooling down to room temperature, 6-bromopyridin-2-yl carboxaldehyde (271 mg, 1.47 mmol, 1.2 equiv) was added and the reaction mixture was stirred at 80 C overnight. The reaction was cooled to room temperature, quenched with brine and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness under vacuum. The product was purified by column chromatography (hexane/ethyl acetate 8:2) to afford the analytically pure compound in 21% yield (80 mg). C13H11BrFNO2; MW 312; 1H NMR (acetone-d6): delta 7.74 (t, J = 7.6 Hz, 1H), 7.64-7.61 (m, 1H), 7.47 (dd, J = 0.9 Hz, J = 7.2 Hz, 1H), 6.92-6.90 (m, 1H), 6.81 (ddd, J = 0.6 Hz, J = 1.3 Hz, J = 9.1 Hz, 1H), 6.59 (dt, J = 2.5 Hz, J = 10.7 Hz, 1H), 5.77 (d, J = 4.7 Hz, 1H), 5.35 (d, J = 4.7 Hz, 1H), 3.79 (s, 3H); 13C NMR (acetone-d6): delta 165.8, 165.3, 140.8, 127.5, 120.3, 109.4, 106.1, 105.9, 101.0, 100.8, 75.8, 56.0; LC/MS m/z: 312-314 (M + H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-fluoro-5-methoxybenzene, its application will become more common.

Reference:
Article; Wetzel, Marie; Gargano, Emanuele M.; Hinsberger, Stefan; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W.; European Journal of Medicinal Chemistry; vol. 47; 1; (2012); p. 1 – 17;,
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 29578-39-0 as follows. COA of Formula: C7H6BrFO

To a suspension of sodium hydride (60% in mineral oil, 600 mg, 15.0 mmol) inDMF (20 mL) at 65 C was slowly added a solution of 4-hydroxy-l -methylpiperidine (1.15 g, 10 mmol) in DMF (7.0 mL). After stirring for 30 minutes, a solution of 3-bromo-5-fluoroanisole (2.05 g, 10 mmol) in DMF (7.0 mL) was added and the reaction mixture was stirred at 65 C for 24 h. The reaction mixture was allowed to cool to ambient temperature then was poured into water (200 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were loaded onto a SCX-2 cartridge, which was then washed with acetonitrile then eluted with 2N ammonia in methanol. Concentration of the basic methanolic fractions in vacuo gave the title compound (1.5 g, 50%). 1H NMR (CDCl3, 400MHz): 6.65 (dd, J = 2.2, 1.6Hz, 1H), 6.63 (dd, J = 2.3, 1.6Hz, 1H), 6.37 (dd, J = 2.3, 2.1Hz, 1H), 4.29-4.21 (m, 1H), 3.75 (s, 3H), 2.70-2.61 (m, 2H), 2.31-2.21 (m, 5H), 2.01-1.93 (m, 2H), 1.86-1.75 (m, 2H). LCMS (Method B): RT = 2.1 min, M+H+ = 300.

According to the analysis of related databases, 29578-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; WO2009/151598; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 29578-39-0, name is 1-Bromo-3-fluoro-5-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 29578-39-0, HPLC of Formula: C7H6BrFO

To a solution of Compound 187 (0.700 g, 3.41 mmol) in 1,4-dioxane (5 ml) were added Compound 188 (0.861 g, 4.10 mmol) and PdCl2(dtbpf) (0.223 g, 0.341 mmol), and then 2 mol/L aqueous solution of potassium carbonate (2.561 ml, 5.12 mmol), and the reaction mixture was stirred at 70C. After completion of the reaction, water was added to the reaction mixture, and the resulting mixture was extracted with chloroform, which was then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain Compound 189 (0.667 g, 93.8%). Compound 189; Method B LC/MS retention time = 1.99 min. MS (ESI) m/z = 209.35(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-fluoro-5-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; Shionogi & Co., Ltd.; TAMURA, Yuusuke; HINATA, Yu; KOJIMA, Eiichi; OZASA, Hiroki; (241 pag.)EP3187498; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 29578-39-0, name is 1-Bromo-3-fluoro-5-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 29578-39-0, Formula: C7H6BrFO

To a solution of 1-bromo-3-fluoro-5-methoxybenzene (15 g, 73.16 mmol), tris(2-methylphenyl)phosphane (1.781 g, 5.85 mmol) and ethyl acrylate (11.90 mL, 109.74 mmol) in TEA (135 mL) was added palladium(II) acetate (0.329 g, 1.46 mmol) under nitrogen gas atmosphere at room temperature, and the mixture was stirred at 90C for 2 days. The solvent was evaporated under reduced pressure, the residue was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give ethyl (E)-3-(3-fluoro-5-methoxyphenyl)acrylate (14.2 g, 63.3 mmol, 87%) as a colorless oil.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, SATOSHI; SHIRAI, JUNYA; WATANABE, HIROYUKI; FUKUMOTO, SHOJI; ODA, TSUNEO; TOKUHARA, HIDEKAZU; TOMATA, YOSHIHIDE; ISHII, NAOKI; TAWADA, MICHIKO; KOUNO, MITSUNORI; OCHIDA, ATSUKO; IMADA, TAKASHI; FUKASE, YOSHIYUKI; YUKAWA, TOMOYA; (719 pag.)TW2016/2105; (2016); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 29578-39-0,Some common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, molecular formula is C7H6BrFO, 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.

A RBF was charged with 1-bromo-3-fluoro-5-methoxybenzene (2.104 g, 10.26 mmol), (3-chlorophenyl)boronic acid (1.765 g, 11.29 mmol), potassium carbonate (4.25 g, 30.8 mmol), and Pd(Ph3P)4 (0.593 g, 0.513 mmol). The flask was flushed with Ar (g), then 1,4-dioxane (25.7 ml) and water (8.55 ml) were added. A reflux condenser was attached, and the flask was lowered into a 90 C. heating bath for 45 min. The mixture was cooled to room temperature, diluted with water, and extracted with EtOAc (2*). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 25-g silica gel column, 0-5% EtOAc/Heptane) to give 3′-chloro-3-fluoro-5-methoxy-1,1′-biphenyl (2.47 g, 10.44 mmol, 102% yield) as a clear oil containing about 10 wt % impurities.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-fluoro-5-methoxybenzene, its application will become more common.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem