Category: 179897-89-3

Electric Literature 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.

General procedure: Into an oven-dried flask equipped with a magnetic stir bar was added aryl fluoride (1.00 g, 1.0 eq.), Na2S (1.1 eq.) and DMF (5 mL) under argon. The reaction mixture was stirred at room temperature for 1 h. Then 1 M NaOH (50 mL) was added and was washed with CH2Cl2 (2 x 25 mL). The aqueous layer was acidified to pH ~ 1-2 with 6 N HCl and extracted with CH2Cl2 (2 x 50 mL). The combined organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide a crude residue. To the residue was added 10% HCl (40 mL) and cooled with an ice-water bath. Then zinc dust (4 g) was added and the mixture was stirred for 1 h. Then EtOAc (100 mL) was added and the mixture was stirred for an additional 30 minutes. The organic layer was separated and washed with water (40 mL) and brine (40 mL), dried over MgSO4, filtered and concentrated to provide the desired product with satisfactory purity.

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

Reference:
Article; Taldone, Tony; Patel, Pallav D.; Patel, Hardik J.; Chiosis, Gabriela; Tetrahedron Letters; vol. 53; 20; (2012); p. 2548 – 2551;,
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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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Bromo-2-fluorobenzonitrile

A mixture of 1-15 (3.0 g, 14.99 mmcl), 1-Boc-piperizine(3.33 g, 17.99 mmcl) and Cs2003 (9.68 g, 29.98 mci) in DMSO(60 ml) was stirred at 12000 for 1 hour. The reaction mixture was diluted with water (100 mL) and extracted with diethyl ether (100 ml x 3) . The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give thedesired product 1-16 (2.5 g, 44%) as yellow solid which wasused in the next step without purification; LCMS: m/z 312 [MtBu+1]

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; NAIK, Keshav; SALUNKHE, Videsh; KULKARNI, Rakesh; PARDESHI, Vishwajeet; BHUNIYA, Debnath; KULKARNI, Bheemashankar; MOOKHTIAR, Kasim Abbaas; (274 pag.)WO2017/38909; (2017); A1;,
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Application of 179897-89-3, 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.

At room temperature,to2-Fluoro-5-bromobenzonitrile (5.0 g)Soluble in ethanol (30mL)80% hydrated hydrazine (7.82g) was added to the solution.After refluxing at 90 C. for 12 h, the reaction solution was cooled to room temperature.Concentrate under reduced pressure to remove the ethanol.The residue was slurried with dichloromethane for 1 h.Filter, wash with dichloromethane, dry,The title compound (5.3 g) was obtained.

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:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Beijing Sai Lintai Pharmaceutical Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; Zhu Li; Hu Yuandong; Dai Liguang; Yang Yanqing; Duan Xiaowei; Yang Zhao; Wu Wei; Sun Yinghui; Han Yongxin; Peng Yong; Luo Huiyan; Luo Hong; Yang Ling; Xu Hongjiang; Guo Meng; Zhong Zhaobo; Wang Shanchun; (102 pag.)CN108003161; (2018); A;,
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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 179897-89-3 as follows. Formula: C7H3BrFN

Add 5-bromo-2-fluoro-benzonitrile (0.5 g, 2.5 mmol), benzophenone imine (0.543 g, 3 mmol), (+-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 60 mg, 0.1 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 50 mg, 0.05 mmol], and Cs2CO3 (1.6 g, 4.9 mmol) in 1,4-dioxane (20 mL). Stir the reaction under N2 at 110 C. 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=1:3) affords the title compound (0.78 g, 99%). MS: (M+1): 301.

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; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); A1;,
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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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 179897-89-3

(1) 5-bromo-2-fluoro-1-cyanobenzene (II, 3 g, 15 mmol) under N2 protection,Sodium sulfide (1.3 g, 16.5 mmol) was reacted in DMF (30 mL) at room temperature for 5 h.Add 300 mL of sodium hydroxide solution (1 mol/L) and stir for 0.5 h.Wash with dichloromethane (300 mL ¡Á 2), acid phase with hydrochloric acid (6 mol / L) to pH = 2, dichloromethane (400 mL ¡Á 2),The combined organic layers were washed with brine, dried over anhydrous magnesium5-bromo-2-thio-1-cyanobenzene (III)1.0 g, yield 31.2%.

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; South China University of Technology; Li Jing; Li Xiaolei; Zhou Haiyan; Wu Fangping; Zhang Lei; (12 pag.)CN108218777; (2018); A;,
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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., Recommanded Product: 5-Bromo-2-fluorobenzonitrile

Referential Example 3 5-Bromo-2-fluorobenzonitrile and piperidine were heated at 80C in DMSO in the presence of cesium carbonate to obtain 5-bromo-2-piperidin-1-ylbenzonitrile. F: 265.

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 179897-89-3.

Reference:
Patent; Astellas Pharma Inc.; EP1783116; (2007); A1;,
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Application 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.

Example 7: 5-Brorno-N-l,3-thiazol-2-yl-lH-indazol-3-amne SCN[0275] Hydrazine monohydrate (2.6 mL, 52.5 mmol) was added to a solution of 5-bromo- 2-fluorobenzonitrile (3.50 g, 17.5 mmol) in ethanol (50 mL) at room temperature. The mixture was stirred for 4 h under reflux condition. After cooling, the mixture was diluted with EtOAc (300 mL), washed with H2O and brine, dried (MgSO4), filtered, and concentrated in vacuo. Purification by recrystallization (EtOAc-hexane) gave 3.37g (91%) of 5-bromo- lH-indazol-3-amine (compound 7A) as a white solid. 1H NMR (300 MHz, CDCl3) delta 4.07 (brs, 2 H) 7.20 (d, IH77=8.85 Hz) 7.42 (dd, IH, J=8.85, 1.70 Hz) 7.71 (d, IH, 7=1.51 Hz) 8.98 (brs, 1 H). MS (ES) [m+H] calc’d for C7H6BrN^, 213; found 211, 213. [0276] Ammonium thiocyanate (229 mg, 3 mmol) was added to a suspension of 5-bromo- lH-indazol-3-amine (212 mg, 1 mmol) in IN hydrochloric acid (3 mL). The mixture was stirred for 4 days at 1000C. The precipitate was collected, and washed with eta2O to give 231 mg (85%) of N-(5-bromo-lH-indazol-3-yI)thiourea (compound 7B) as a yellow solid. 1H NMR (300 MHz, DMSO-rf6) delta 7.43 (d, IH, 7=8.85 Hz) 7.50 (dd, IH, 7=8.85, 1.88 Hz) 8.49 (d, IH, 7=1.32 Hz) 8.79 (brs, IH) 9.18 (brs, IH) 10.85 (s, IH) 12.86 (s, IH). MS (ES) [m+H] calc’d for C8H7BrN4S, 272; found 270, 272.[0277] To a stirred solution of N-(5-bromo-lH-indazol-3-yl)thiourea (104 mg, 0.38 mmol) in ethanol (2 mL) and H2O (1 mL) was added 1 ,2-dichloroethyl ethyl ether (0.05 mL, 0.41 mmol) at room temperature. The mixture was stirred for 3 h at 8O0C. After dilution with EtOAc, the organic layer was washed with H2O and brine, dried (MgSO4), filtered, and concentrated in vacuo. Crystallization from EtOAc-diisopropyl ether gave 62.7 mg (55%) of 5-Bromo-N-l,3-thiazol-2-yl-lH-indazol-3-amine (compound 7) as a white solid. 1H NMR (300 MHz, DMSO-^6) delta 7.01 (d, IH, 7=3.58 Hz) 7.36 (d, IH, 7=3.58 Hz) 7.37 – 7.42 (m, IH) 7.44 – 7.49 (m, IH) 8.35 (d, IH, 7=1.32 Hz) 11.34 (brs, IH) 12.53 (s, IH). MS (ES) [m+H] calc’d for C10H7BrN4S, 296; found 294, 296.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA SAN DIEGO, INC.; WO2007/75847; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H3BrFN

5-Bromo-2-fluorobenzonitrile (53) (500 mg, 2.54 mmol) was coupled to phenylboronic acid (335 mg, 2.75 mmol) with Cs2CO3 (1.63 g, 5.00 mmol) in toluene (4 mL) in a microwave at 140 C. for 30 minutes. Water was added and the organics extracted several times with EtOAc, dried (MgSO4), filtered and the solvent concentrated in vacuo. The crude product was purified by Flash Master Jones Chromatography using a 25 g silica cartridge and eluting with 10% EtOAc in heptane to yield the title compound. Yield: 375 mg, 76%; LC-MS 41.63 min; HPLC Purity: 97%; MS (ES+) m/z not detectable (M+H)

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

Reference:
Patent; ASTERAND UK LIMITED; US2010/130556; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature 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.

To a solution of zinc chloride (50 mL, 1.0 M in diethyl ether, 50 mmol) was added neopentylmagnesium chloride (50 mL, 1.0 M in THF, 50 mmol) dropwise at 0 C. During the addition, the generated magnesium salts formed a white precipitate. The reaction was removed from the ice bath and allowed to stir for 1 h then 1-bromo-2-fluorobenzonitrile (5 g, 25 mmol) was added followed by bis (tri-tert- butylphosphine) palladium (0.127 g, 0.25 mmol, 1%). The reaction began to reflux and was placed back into the ice bath. After 1 h, the reaction was diluted with 200 mL of diethyl ether and washed with 1 N HCI (2 x 100 mL), brine (100 mL), dried over magnesium sulfate and concentrated to give an oily solid (4.3 g, 22 mmol, 90%).

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; ELAN PHARMACEUTICALS, INC.; WO2005/70407; (2005); 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., Recommanded Product: 179897-89-3

To a solution of zinc chloride (50 mL, 1. OM in diethyl ether, 50 mmol) was added neopentylmagnesium chloride (50 mL, 1. OM in THF, 50 mmol) dropwise at 0 C. During the addition, the generated magnesium salts formed a white precipitate. The reaction was removed from the ice bath and allowed to stir for 1h, then 1- bromo-2-fluorobenzonitrile (5 g, 25 mmol) was added followed by bis (tri-tert- butylphosphine) palladium (0.127 g, 0.25 mmol, 1%). The reaction began to reflux and was placed back into the ice bath. After 1 h, the reaction was diluted with 200 mL of diethyl ether and washed with 1N HCI (2 x 100 mL), brine (100 mL), dried over magnesium sulfate and concentrated to give an oily solid (4.3 g, 22 mmol, 90%). H NMR (400 MHz, CDC13) 8 7.38-7. 30 (m, 2H), 7.11 (dt, J=8.5, 1.4 Hz, 1 H), 2.49 (s, 2H), 0.90 (s, 9H).

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 179897-89-3.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87751; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts