Category: 38197-43-2

Synthetic Route of 38197-43-2, A common heterocyclic compound, 38197-43-2, name is 2-Bromo-1-methoxy-3-methylbenzene, molecular formula is C8H9BrO, 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: 2-methoxy-6-methylbenzonitrile: To a flask containing a stir bar was added 2-bromo-l- methoxy-3-methylbenzene (7.5 g, 37 mmol), CuCN (6.7 g, 75 mmol) followed by addition of DMF (60 mL); the resulting mixture was then refluxed at 150 C overnight. When the reaction was complete, as evidenced by LC analysis, the reaction flask was taken out of the oil bath and cooled to room temperature. To the reaction mixture was then poured DCM (20 mL) and a precipitate formed immediately. The solids were filtered, re-dissolved in DCM, absorbed into silica gel and and loaded into column with Hexanes:EtOAc (1 : 1) to afford the title product.

The synthetic route of 38197-43-2 has been constantly updated, and we look forward to future research findings.

Some common heterocyclic compound, 38197-43-2, name is 2-Bromo-1-methoxy-3-methylbenzene, molecular formula is C8H9BrO, 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. Formula: C8H9BrO

General procedure: A mixture of 17 (200 mg, 0.369 mmol), 2-bromo-1-methoxy-3-methylbenzene(148 mg, 0.737 mmol), Pd(OAc)2 (8.3 mg, 0.037 mmol), 2-dicyclohexylphosphino-2?,6?-di-isopropoxy-1,1?-biphenyl (34.4 mg,0.074 mmol), and Cs2CO3 (360 mg, 1.11 mmol) in toluene (7.5 ml) and water (1.5 ml) was stirred at 80 C for 25 h. Then, water was added tothe reaction mixture, and the product was extracted with AcOEt. Theorganic layer was successively washed with water and brine, dried overanhydrous Na2SO4 and concentrated in vacuo. The residue was purifiedby silica gel column chromatography (hexane/AcOEt=40/60 to 10/90) to give the title compound as a white solid (43 mg, 21%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 38197-43-2, its application will become more common.

Reference:
Article; Murafuji, Hidenobu; Sugawara, Hajime; Goto, Megumi; Oyama, Yoshiaki; Sakai, Hiroki; Imajo, Seiichi; Tomoo, Toshiyuki; Muto, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3639 – 3653;,
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Ether | (C2H5)2O – PubChem

Application of 38197-43-2, These common heterocyclic compound, 38197-43-2, name is 2-Bromo-1-methoxy-3-methylbenzene, 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.

General procedure: To a mixture of 1-bromo-2-methoxynaphthalene (2.3mmol) and magnesium turnings (9.0mmol) in diethyl ether (10mL) was stirred at room temperature under argon atmosphere until white slurry was formed. To the resulting mixture was added benzene (10mL) to dissolve the material, and the mixture was stirred for 2h at room temperature under argon atmosphere. The solution of resulting Grignard reagent was added dropwise to a solution of 2-methoxy-1,3-dinitrobenzene (1.5mmol) in benzene (15mL), and the mixture was stirred for 8h at 50C. The reaction mixture was quenched with water and extracted with ethyl acetate (3¡Á15mL). The combined extracts were dried over Na2SO4, and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane as eluent) to give a precursor of the starting material, which was the corresponding dinitro compound (1.1mmol, 73% yield). A mixture of the corresponding dinitro compound (1.0mmol) and Pd/C (80mg; 10wt%) in ethanol (10mL) was stirred for 12h at room temperature under hydrogen atmosphere (H2 balloon). The reaction mixture was filtered over Celite and concentrated to give a diamino compound. To a solution of the resulting diamino compound and pyridine (30mmol) in dichloromethane (20mL) was added dropwise a solution of benzenesulfonyl chloride (3.0mmol) in dichloromethane (10mL), and the reaction mixture was stirred for 24h at room temperature. The mixture was concentrated, and the residue was purified by column chromatography on silica gel (dichloromethane/ethyl acetate/hexane as eluent) to give starting material 8a (0.98mmol, 98% yield). Compounds 8b and 8c were synthesized by the same procedure.

The synthetic route of 38197-43-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shirakawa, Seiji; Wu, Xiangfei; Liu, Shiyao; Maruoka, Keiji; Tetrahedron; vol. 72; 34; (2016); p. 5163 – 5171;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 38197-43-2, 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 38197-43-2 as follows.

To a solution of 2-bromo-1-methoxy-3-methylbenzene (Combi-Blocks CAS No.38197-43-2) (1.024 g, 5.09 mmol) in tetrahydrofuran (25.5 mL) was added bis(dibenzylideneacetone)palladium (0.059 g, 0.102 mmol) and Q-Phos (1,2,3,4,5-Pentaphenyl-1′-(di-tert-butylphosphino)ferrocene) (pentaphenyl(di-tert-butylphosphino)ferrocene, 0.072 g, 0.102 mmol). Nitrogen was bubbled through the solution for about 3 minutes, then a 0.4 M in tetrahydrofuran solution of (1-(methoxycarbonyl)cyclopropyl)zinc(II) bromide (25.5 mL, 10.19 mmol) was added dropwise over 5 minutes and the internal temperature rose from 23.5 C. to 24.8 C. The reaction was stirred for 15 hours at ambient temperature, at which point it was quenched with saturated aqueous ammonium chloride (30 mL), diluted with methyl tert-butyl ether (130 mL), and the layers were separated. The organic layer was filtered through a pad of silica gel. The filtrate was concentrated in vacuo to give a crude residue that was purified via flash chromatography, eluting on a 40 g silica gel cartridge with 1-40% ethyl acetate/heptanes over 40 minutes to provide the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 7.15 (t, J=7.9 Hz, 1H), 6.76-6.80 (m, 1H), 6.73 (d, J=8.2 Hz, 1H), 3.80 (s, 3H), 3.60 (s, 3H), 2.32 (s, 3H), 1.71-1.75 (m, 2H), 1.54 (s, 2H)+ MS (ESI+) m/z 221 (M+H)+, 243 (M+Na)+.

According to the analysis of related databases, 38197-43-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; Desroy, Nicolas; Gfesser, Gregory A.; Housseman, Christopher Gaetan; Kym, Philip R.; Liu, Bo; Mai, Thi Thu Trang; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Picolet, Olivier Laurent; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; (189 pag.)US2019/77784; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 38197-43-2, name is 2-Bromo-1-methoxy-3-methylbenzene, 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 38197-43-2, Computed Properties of C8H9BrO

To a solution of 2-bromo-3-methylphenol (10.0 g, 53.5 mmol) in DMF (60 ml) was added sodium hydride (2.78 g, 69.5 mmol) in small portions at 0 C, which was followed by addition of Mel (6.69 mL, 107 mmol). TLC showed formation of a slightly less polar spot right away. The reaction was diluted with EtOAc (400 mL), washed with water 3 times, dried over Na2S04, and concentrated. The crude product was used in the next step without further purification. To the flask charged with the above material and a stir bar was added CuCN (9.9 g, 109 mmol) and DMF (100 mL). The mixture was purged three times with nitrogen, and heated to 150 C for 24 hours. TLC showed formation of a more polar spot. . The reaction was cooled to RT, diluted with DCM (400 mL), and filtered through a pad of celite to remove the solids. The filtrate was washed with saturated NH4Oac and brine, dried over sodium sulfate, concentrated to afford a brownish solid (4.8g, 60% yield). The resulting nitrile was used in the following step without further purification. To a flask charged with the nitrile and a stir bar was added NBS (6.4 g, 36 mmol) and TFA (60 mL). The reaction was allowed to stir at RT for 16 hours. TLC showed clean formation of a slightly more polar spot. The solvent was removed under vacuum, and the residue was purified by silica gel flash chromatography. After removal of solvent, 3-bromo-6-methoxy-2-methylbenzonitrile was collected.

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Reference:
Patent; MERCK SHARP & DOHME CORP.; PIO, Barbara; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; WALSH, Shawn; WO2013/90271; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem