Category: 179897-89-3

Synthetic Route of 179897-89-3,Some common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Add 5-bromo-2-fluoro-benzonitrile (0.5 g, 2.5 mmol), benzophenone imine (0.543 g, 3 mmol), (¡À)-2,2′-bis(diphenylphosphino)-l,l’-binaphthalene (BetaGammaNuAlphaRho, 60 mg, 0.1 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 50 mg, 0.05 mmol], and Cs2C03 (1.6 g, 4.9 mmol) in 1,4-dioxane (20 mL). Stir the reaction under N2 at 110C for 16 hrs. Cool to room temperature, filter the solid, and concentrate the filtrate to give the crude product. Purification by chromatography (silica gel, EtOAc_PE=l :3) affords the title compound (0.78 g, 99%). MS: (M+1): 301.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-fluorobenzonitrile, its application will become more common.

Reference:
Patent; CROWN BIOSCIENCE INC. (TAICANG); ZHANG, Deyi; ZHANG, Ruihao; ZHONG, Boyu; SHIH, Chuan; WO2014/418; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, belongs to nitriles-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 179897-89-3, Safety of 5-Bromo-2-fluorobenzonitrile

To 5-Bromo-2-fluoro-benzonitrile (10.05 g, 50.25 mmol) in DMSO (30 mL) is added sodiummethanethiolate (3.87 g, 55.27 mmol) portionwise at 0 C. The reaction mixture is stirred for 2 h at r.t. Sodiummethanethiolate (1.06 g, 15.07 mmol) is added and stirred for further 2 h at r.t. The reaction mixture is diluted with water (100 mL) and the precipitate is filtered off and dried in vacuo at 50 C. [0325] Yield 88% m/z 228/230 [M+H]+, rt 1.26 min, LC-MS Method V018_S01

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275159; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 179897-89-3,Some common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

5-Bromo-2-(2,2-dimethyl-butoxy)benzonitrile; Sodium hydride (60% oily) (2.0 g, 50.0 mmol) was gradually added to a solution of 5-bromo-2-fluorobenzonitrile (5.0 g, 25.0 mmol) and 2,2-dimethylbutan-1-ol (5.1 g, 50.0 mmol) in anhydrous DMF (100 mL) at 0C. After stirring at room temperature for 15 hours, the reaction mixture was poured into ice water followed by extracting with ethyl acetate. The organic layer was washed with a saturated saline solution and then dried. The residue prepared by evaporation of the solvent was purified by silica gel column chromatography (hexane/ethyl acetate = 50/1) to give the title compound (6.2 g, 88%) as an oily product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-fluorobenzonitrile, its application will become more common.

Reference:
Patent; Nippon Zoki Pharmaceutical Co., Ltd.; EP2128136; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 179897-89-3, These common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, 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: A mixture of compound 1 (5.0 mmol), alkylamine (15.0 mmol),and K2CO3 (15.0 mmol) in DMF (10 mL) was reacted at 70e80 C for3e5 h. After the reaction was complete, the mixture was pouredinto H2O (100 mL) and extracted with ethyl acetate (100 mL 2).The organic layer was collected, washed with brine (100 mL 3),dried over anhydrous Na2SO4, and concentrated under vacuum toyield the crude product, which was purified by flash columnchromatography (0e15% ethyl acetate in petroleum ether).

The synthetic route of 179897-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Haiyan; Li, Xiaolei; Li, Yuanyuan; Zhu, Xinying; Zhang, Lei; Li, Jing; European Journal of Medicinal Chemistry; vol. 186; (2020);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 179897-89-3,Some common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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 5-Bromo-2-fluoro-bcnzonitrile (1 0.05 g, 50.25 mmol) in DMSO (30mL) is addedsodiummetl1anethiolate (3.87 g, 55.27 mmol) portionwise at 0C. The reaction mixture is stirred for2h at r.t..Sodiummethanethiolate ( l.06g, 15.07 mmol) is added and stirred for further 2h at r.t ..The reaction mixture is diluted with water (1 00 mL) and the precipitate is filtered off and dried invacuo at 50C. Yield 88% m/z 228/230 [M+H]+, rt 1.26 min, LC-MS Method V018_S01.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-fluorobenzonitrile, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140081; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 179897-89-3, A common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

5-bromo-2-fluoro-benzonitrile (12.4 mmol, 2470 mg) in pyridine (6.5 mL) was treated with ammonium sulfide (40 mass% in water, 1.1 equiv., 13.6 mmol, 2.32 mL) and triethylamine (1.1 equiv. , 13.6 mmol, 1.90 mL). The reaction mixture was heated at 50 C for 3 hours, then cooled to room temperature. The reaction mixture was partitioned between EtOAc and water. The organic later was washed with water (3x), and brine (3x), dried with MgS04, then concentrated. The residue was purified on silica eluted with 0 to 50% EtOAc in Heptane to provide 5-bromo-2-fluoro-benzenecarbothioamide (2.84 g, 94% yield). A mixture of 5-bromo-2-fluoro-benzenecarbothioamide (11.8 mmol, 2840 mg) and ethyl bromopyruvate (1.05 equiv., 12.4 mmol, 1.56 mL) in ethanol (30 mL) was heated at 80 C overnight. The mixture was concentrated and the residue was purified on silica eluted with 0 to 20% EtOAc in Heptane to afford ethyl 2-(5-bromo-2-fluoro-phenyl)thiazole-4- carboxylate (2960 mg, 76.14% Yield) as a clear oil. To a solution of ethyl 2-(5-bromo-2-fluoro-phenyl)thiazole-4-carboxylate (8.97 mmol, 2960 mg) in methanol (40 mL) and water (10 mL) was added lithium hydroxide (1.6 equiv., 14.2 mmol, 347 mg) . The reaction mixture was stirred at 50 C for 2 hours. The reaction mixture was cooled to room temperature, concentrated, suspended in water, and then quenched with 2N HCl(aq.). The solid was collected, washed with water, and dried under high vacuum to afford 2-(5-bromo-2-fluoro-phenyl)thiazole-4-carboxylic acid (2410 mg, 89% Yield) as a white solid. -(6-(trifluoromethyl)pyridin-2-yl)thiazole-4-carboxylic acid

The synthetic route of 179897-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BURCH, Jason; CHEN, Huifen; WANG, Xiaojing; WO2015/140189; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

The title compound was prepared by a modification of the literature procedure as described in Palermo, M. G., Tetrahedron Lett, 37:2885 (1996). A single neck 50 mL flask equipped with a magnetic stirred was charged with N-hydroxyacetamide (2.63 g, 35.0 mmol) and DMF (100 mL). Then, KOtBu (3.93 g, 35.0 mmol) was added in one portion. The temperature rose to 300C. The mixture was stirred for Ih and, 5-bromo~2-fluorobenzonitrile (7 g, 35.0 mmol) was added. The reaction mixture was stirred for overnight. A further portion of KOtBu (1.96 g, 17.5mmo) was added and the solution was again stirred overnight. The mixture was poured into brine and CH2CI2 and the layers were separated. The organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash column chromatography (BIOTAGE, eluting with a gradient of 0 to 40% EtOAc in hexanes) to afford the title compound (4.59 g, 62%) as a colorless solid. 1H NMR (500 MHz, DMSOd6) delta 8.09 (d, J = 1.8 HZ, IH), 7.65 (dd, J = 2.1, 8.9 Hz, IH), 7.45 (d, J = 8.9 Hz5 IH), 6.49 (s, 2H). LCMS: Anal. Calcd. for C7H5BrN2O: 2115 213; found: 212, 214 (M+H)+.

According to the analysis of related databases, 179897-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAVOIE, Rico; JAMES, Clint A.; RUEDIGER, Edward H.; WO2010/138488; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, belongs to nitriles-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. 179897-89-3

5-bromo-2-fluorobenzonitrile (1.0 g, 5.0 mmol) was weighed and dissolved in DMF (10 mL), Add K2CO3 (2.1 g, 15.0 mmol), stir at room temperature for 1.0 h, add N-methylisobutylamine (1.3 g, 15.0 mmol), and react at 80 C for 3 h. TLC followed the reaction completely.Cooled to room temperature, diluted with 100mL of water was added, ethyl acetate (100mL ¡Á 3). The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, purification by silica gel column (V ethyl acetate: V petroleum ether = 1: 20) afforded 5-bromo-2-isobutylmethylaminobenzonitrile (a10)1.27 g, yield 95%

Statistics shows that 179897-89-3 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-fluorobenzonitrile.

Reference:
Patent; South China University of Technology; Li Jing; Li Xiaolei; Li Yuanyuan; Zhou Haiyan; Zhang Lei; Guan Su; (21 pag.)CN110078668; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 179897-89-3 name is 5-Bromo-2-fluorobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 179897-89-3

General procedure: A mixture of compound 1 (5.0 mmol), alkylamine (15.0 mmol),and K2CO3 (15.0 mmol) in DMF (10 mL) was reacted at 70e80 C for3e5 h. After the reaction was complete, the mixture was pouredinto H2O (100 mL) and extracted with ethyl acetate (100 mL 2).The organic layer was collected, washed with brine (100 mL 3),dried over anhydrous Na2SO4, and concentrated under vacuum toyield the crude product, which was purified by flash columnchromatography (0e15% ethyl acetate in petroleum ether). 4.1.1.1. 5-Bromo-2-(isobutyl(methyl)amino)-benzonitrile (2a).Yellow oil (yield: 93%); 1H NMR (400 MHz, CDCl3) d 7.54 (d, 1H,J 1.3 Hz, ArH), 7.42 (dd, 1H, J 9.1, 3.3 Hz, ArH), 6.75 (d, 1H,J 9.1 Hz, ArH), 3.19 (d, 2H, J 7.5 Hz, -NCH3CH2CH(CH3)2), 3.05 (s,3H, -NCH3CH2CH(CH3)2), 2.01 (m,1H, eNCH3CH2CH(CH3)2), 0.89 (d,6H, J 6.6 Hz, eNCH3CH2CH(CH3)2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Zhou, Haiyan; Li, Xiaolei; Li, Yuanyuan; Zhu, Xinying; Zhang, Lei; Li, Jing; European Journal of Medicinal Chemistry; vol. 186; (2020);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding some certain compound to certain chemical reactions, such as: 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, 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 179897-89-3. 179897-89-3

a) 5-Bromo-2-(4-methyl-imidazol-1-yl)-benzonitrile A mixture of 5-bromo-2-fluoro-benzonitrile (25.0 g, 125 mmol), 4-methylimidazole (12.5 g, 152 mmol), potassium carbonate (34.55 g, 250 mmol) in DMSO (500 mL) was stirred at 90 C. for 16 h. Water (1.5 L) was added and the resulting suspension was stirred with ice-bath cooling for 1 h. The precipitate was filtered, washed with water (0.5 L) and dried at 50 C. over KOH. The resulting raw material (25.6 g) was dissolved in boiling Ethyl acetate (300 ml). After addition of diisopropylether (300 ml) the solution was allowed to cool to room temperature. Filtration and drying afforded the title compound (19.35 g, 59%) as a white solid. Mp 166 C.

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 5-Bromo-2-fluorobenzonitrile.

Reference:
Patent; Buettelmann, Bernd; Knust, Henner; Thomas, Andrew William; US2006/128691; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts