Author: tianli

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. 135748-35-5, name is 4-Chloro-2,5-difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Chloro-2,5-difluorobenzonitrile

b [3-(5-Chloro-2-cyano-4-fluorophenoxy)-4-pentenyl]methylcarbamic Acid, 1,1-dimethylethyl Ester The subtitle compound was prepared according to the method of Example 3 step (b) using (3-hydroxy-4-pentenyl)methylcarbamic acid, 1,1-dimethylethyl ester and 4-chloro-2,5-difluorobenzonitrile in N,N-dimethylformamide. 1H NMR 300 MHz (CDCl3) 7.33 (1H, d), 7.00 (1H, d), 5.85 (1H, m), 5.30 (2H, m), 4.65 (1H, m), 3.35-3.51 (2H, m), 2.87 (3H, s), 1.97-2.10 (2H, m), 1.41 (9H, s).

According to the analysis of related databases, 135748-35-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; US2003/65174; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 179898-34-1, 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 179898-34-1 as follows.

Example 54 3 ‘-({ [(1 ,1-Dimethylethyl)(dimethyl)silyl] oxy} methyl)-5-fluoro- 3- biphenylcarbonitrile3-bromo-5-fluorobenzonitrile (5.00 g, 25.0 mmol), Pd(OAc)2 (0.15 g), PPh3 (0.60 g) and K2CO3 (5.18 g, 37.5 mmol) were dissolved in dioxane (60 mL). The mixture was heated at 700C for 30 min, then [3 -({[(l,l-dimethylethyl)(dimethyl)silyl] oxy} methyl) phenyljboronic acid (7.99 g, 30.0 mmol) was added. The mixture reaction was stirred at reflux overnight. The solvent was removed under reduced pressure, then diluted with CH2Cl2 (100 mL). The organic layer was washed with water (50 mL) and brine (50 mL). And the organic layer was dried over Na2SOzI. The product 3’-({[(l,l-dimethylethyl) (dimethyl)silyl]oxy} methyl)-5-fluoro-3-biphenylcarbonitrile (5.10 g, 60%) was purified by flash column chomatography. 1H NMR (400 MHz, CDCl3) delta 7.67 (t, J=5.2 Hz, 1 H), 7.54-7.32 (m, 5 H), 4.81 (s, 2 H), 0.94 (s, 9 H), 0.13 (s, 6 H).

According to the analysis of related databases, 179898-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/100169; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, 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 2338-75-2, category: nitriles-buliding-blocks

A solution of 5.0 g (27 mmol) of 4-(trifluoromethyl)phenylacetonitrile in 60 mL 2 M MeOH / NH3 was treated with 0.7 g of Raney Nickel. The mixture was then shaken on a Parr Apparatus under 50 psi of hydrogen for 18 h. The mixture was filtered through celite and the filtrate was concentrated in vacuo to afford 4.62 g of the product amine as brown oil. 1H NMR (CDC13, 400 MHz) 8:7.56-7.58, (d, 2H), 7.32- 7.34 (d, 2H), 3.00 (t, 2H), 2.8 (t, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Trifluoromethyl)phenylacetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2005/110409; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, 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 170572-49-3, Quality Control of 3-Fluoro-4-methylbenzonitrile

Example 11A 3-Fluoro-4-formylbenzonitrile The reaction was carried out under argon. 3-Fluoro-4-methylbenzonitrile (121 g, 895 mmol) and N,N-dimethylformamide dimethylacetal (245 g, 2.06 mol) were dissolved in DMF (1.8 liters) and stirred under reflux overnight. The content of the flask was then poured into water (2 liters), the mixture was extracted twice with ethyl acetate and the combined organic phases were washed with saturated sodium chloride solution. The organic phase was concentrated and the residue was redissolved in THF/water (1:1, 2.7 liters). Sodium periodate (503 g, 2.35 mol) was added, and the mixture was stirred at room temperature for one hour. The precipitate was then removed and the filtrate was recovered and extracted repeatedly with ethyl acetate. The combined organic phases were washed once with saturated sodium bicarbonate solution and once with saturated sodium chloride solution, dried and concentrated to give an oil. This oil was purified by column chromatography on silica gel (mobile phase: petroleum ether/dichloromethane 6:4, then 4:6, finally pure dichloromethane). The product fractions were concentrated. This gave 28.0 g (20% of theory) of the target compound as a white crystalline solid. GC-MS (Method 1): Rt=3.63 min; MS (ESIpos): m/z (%)=149.0 (48) [M]+, 150.0 (5) [M+H]+ 1H-NMR (400 MHz, DMSO-d6): delta=7.89 (d, 1H), 8.00 (t, 1H), 8.11 (d, 1H), 10.24 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Fluoro-4-methylbenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/94968; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 115661-37-5,Some common heterocyclic compound, 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, molecular formula is C7H5FN2, 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) N-(2-cyano-6-fluorophenyl)-3-oxobutanamide (0714) To a mixture of 2-amino-3-fluorobenzonitrile (41.9 g), sodium acetate (30.3 g) and toluene (200 mL) was added diketene (28.2 mL) at 0C over 10 min. The reaction mixture was stirred at room temperature for 7 hr. To the reaction mixture were sequentially added toluene (150 mL) and diketene (4.7 mL) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was recrystallized from diisopropyl ether/ethanol to give the title compound (48.64 g). MS (ESI+): [M+H]+ 221.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-3-fluorobenzonitrile, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOSHIDA, Masato; NAGAMIYA, Hiroyuki; OHBA, Yusuke; SETO, Masaki; YOGO, Takatoshi; SASAKI, Satoshi; TOKUNAGA, Norihito; ASO, Kazuyoshi; (298 pag.)EP2980089; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 63069-50-1, 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 63069-50-1 as follows.

4-Amino-3-chloro-5-fluorobenzonitrile A mixture of 4-amino-3-fluorobenzonitrile (1 equiv.) and N-chlorosuccinimide (1.5 equiv.) in acetonitrile (0.24 M) was stirred at 85 C. for 5 h. The solvent was removed by concentration and the residue was partitioned between ethyl acetate and 5% NaOH. The organic phase was washed with 5% NaOH and brine. Then the organic phase was dried over MgSO4 and dried in vacuum to afford 4-amino-3-chloro-5-fluorobenzonitrile (88%) as a beige solid. 1H NMR (400 MHz, CDCl3) delta ppm: 7.41 (t, J=6 Hz, 1H), 7.24 (dd, J=1.8, 10.2 Hz, 1H), 4.66 (s, 2H).

According to the analysis of related databases, 63069-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Signal Pharmaceuticals, LLC; Alexander, Matthew; Bahmanyar, Sogole; Hansen, Joshua; Huang, Dehua; Hubbard, Robert; Jeffy, Brandon; Leisten, Jim; Moghaddam, Mehran; Raheja, Raj K.; Raymon, Heather; Schwarz, Kimberly; Sloss, Marianne; Torres, Eduardo; Tran, Tam Minh; Xu, Shuichan; Zhao, JingJing; Boylan, John Frederick; (317 pag.)US2016/96841; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 778-94-9, 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. 778-94-9, name is 2-Nitro-4-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2. Synthesis of intermediate Compound 3To a solution of SnCl2 (3.34 g, 14.8 mmol) in concentrated HC1 (2.7 mL) was added a solution of compound 2 (0.8 g, 3.7 mmol) in 95% ethanol (1.3 mL). The resulting mixture was stirred at room temperature for 2 h. TLC showed the reaction was completed, and the mixture was treated with 50% aqueous NaOH solution (10 mL) to give the yellow solid. The resulting mixture was filtered, and the filter cake was dissolved in CH2C12 (200 mL). The mixture was filtered, and the filtrate was dried over Na2S04 and concentrated in vacuo to give compound 3 (0.4 g, 58%>) as a yellow solid.

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, 2-Nitro-4-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DILLARD, Lawrence W.; YUAN, Jing; LEFTHERIS, Katerina; VENKATRAMAN, Shankar; WU, Guosheng; JIA, Lanqi; XU, Zhenrong; CACATIAN, Salvacion; MORALES-RAMOS, Angel; SINGH, Suresh; ZHENG, Yajun; WO2011/106414; (2011); A1;,
Nitrile – Wikipedia,
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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. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Product Details of 621-50-1

To a solution of 3 (400.0 mg, 2.47 mmol) in anhydrous THF (5 mL) was slowly added a suspension of 60% sodium hydride in mineral oil (641.4 mg, 16.03 mmol) in anhydrous THF (4.2 mL) under argon at 0 C. Methyl iodide (1.23 mL, 19.74 mmol) was added to the mixture. The temperature was allowed to rise to room temperature and stirred for 16 h. After being quenched by the addition of water, the aqueous layer was extracted with EtOAc (2 ¡Á 15 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered. The residue was purified by column chromatography on silica gel (EtOAc/hexane, 5:95 to 10:90) to afford 4 (141.3 mg, 30%) as a brown solid; 1H NMR (CDCl3, 400 MHz) 8.31 (1 H, t, J = 2.3 Hz), 8.21-8.19 (1 H, m), 7.90-7.87 (1 H, m), 7.61 (1 H, t, J = 7.8 Hz), 1.79 (6 H, s); 13C NMR (CDCl3, 100 MHz) 148.5, 143.5, 131.6, 130.1, 123.3, 123.0, 120.1, 37.1, 28.9.

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:
Article; Suebsuwong, Chalada; Pinkas, Daniel M.; Ray, Soumya S.; Bufton, Joshua C.; Dai, Bing; Bullock, Alex N.; Degterev, Alexei; Cuny, Gregory D.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 4; (2018); p. 577 – 583;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, molecular formula is C5H5NO, 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. Quality Control of 3-Oxocyclobutanecarbonitrile

into a 500-mL round-bottom flask, was placed a solution of 3-oxocyclobutane-l-carbonitrile (4 g, 42.06 mmol, 1.00 eq.) tetra(propan-2-yloxy)titanium (14.16 g, 62.90 mmol, 1.50 eq.) and 2- methylpropane-2-sulfinamide (6.12 g, 50.49 mmol, 1.20 eq.) in tetrahydrofuran (200 mL). The resulting solution was stirred for 16 hours at 65C. The reaction was cooled to 25C. Then NaBH4 (3.2 g, 84.60 mmol, 2.00 eq.) was added. The mixture was stirred for 2 hours at 25C. The reaction was then quenched by the addition of 200 mL of water. The solids were filtered out and the resulting solution was extracted with ethyl acetate (2×200 mL) and the organic layers were combined. The resulting mixture was washed with brine (2×300 mL), dried over sodium sulfate and concentrated under vacuum. This resulted in 7.2 g (85%) of N-(3- cyanocyclobutyl)-2-methylpropane-2-sulfinamide as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20249-16-5, its application will become more common.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (178 pag.)WO2016/115090; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, 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 3759-28-2, name: 2-(Cyanomethyl)benzonitrile

General procedure: A mixture of 1-aryl/alkyl-3,3-bis-methylsulfanyl-propenone (1.0 mmol), 2-cyanomethyl-benzonitrile (1 mmol, 142.0 mg), and powdered KOH (2 mmol, 112.0 mg) in dry DMSO (5 mL) was stirred at room temperature for 2 h. Completion of reaction was monitored by TLC. After completion, reaction mixture was poured onto ice-water with constant stirring and then neutralized with 10% HCl. The precipitate obtained was filtered, washed with water and dried over dry sodium sulfate. Many compounds were purified by recrystallization in dry methanol. Some compounds were purified through column chromatography using 15% ethylacetate in hexane as an eluent. Characterization data for some of the synthesized compounds are reported earlier.17

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

Reference:
Article; Singh, Surjeet; Althagafi, Ismail; Yadav, Pratik; Panwar, Rahul; Kumar, Abhinav; Pratap, Ramendra; Tetrahedron; vol. 70; 46; (2014); p. 8879 – 8884;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts