Author: Jessica.F

Application of 50712-68-0, A common heterocyclic compound, 50712-68-0, name is 4-Chloro-2-methylbenzonitrile, molecular formula is C8H6ClN, 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 4-Chloro-2-(bromo-methyl)-benzonitrile 2 To a stirred solution 4-Chloro-2-methyl-benzonitrile 1(5.0 g, 33.0 mmol) in carbon tetrachloride (150 mL) was added N-bromosuccinamide (7.6 g, 42.9 mmol) and 2,2′-azobisisobutyronitrile (cat.). The reaction mixture was refluxed 6 hrs, filtered, concentrated, and partitioned between ether and water. The ether layer was dried, concentrated, and purified by silica gel chromatography (10% ether/hexanes) to yield a white solid (40%). 1H NMR (400 MHz, CDCl3) delta7.61 (d, J=8.3 Hz, 1 H, Ar), 7.57 (d, J=2.2 Hz, 1 H, Ar), 7.41 (dd, J=8.3, 2.0 Hz, 1 H, Ar), 4.59 (s, 2 H, CH2).

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; Merck & Co., Inc.; US6376530; (2002); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 243128-37-2

To a stirred solution of trans-4-aminocyclohexanol (115 mg, [1] mmol) in DMF (5 mL) at 0 [C] was added 60% NaH in mineral oil (120 mg, 3 [MMOL).] The reaction mixture was stirred at 0 [C] for 1/2 hour and then 4-fluoro-3-methoxy-benzonitrile (182 mg, 1.2 mmol) was added. It was heated to 60 [C] for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) [M/Z] 247 (M+H) [+.]

The synthetic route of 243128-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/26822; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 134227-45-5,Some common heterocyclic compound, 134227-45-5, name is 3,4,5-Trifluorobenzonitrile, molecular formula is C7H2F3N, 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.

Potassium carbonate (1.38 g, 10 mmol) was added to a solution of 2,4-dihydro- 2,5-dimethyl-3H-pyrazol-3-one (0.70 g, 6.3 mmol) in N,N-dimethylformamide (15 mL). 3,4,5-Trifluorobenzonitrile (0.94 g, 6.0 mmol) was added, and the reaction mixture was heated at 75 C under a nitrogen atmosphere for 16 h, then allowed to cool. The reaction mixture was partitioned between water (60 mL) and ethyl acetate (30 mL). The organic phase was washed with water (2 x 30 mL) and brine (30 mL), dried over MgS04, and concentrated to give the title compound as a yellow oil (1.38 g).¾ NMR delta 7.36 (m, 2H), 5.24 (s, 1H), 3.78 (s, 3H), 2.16 (s, 3H).

The synthetic route of 134227-45-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; LONG, Jeffrey, Keith; GREGORY, Vann; GUTTERIDGE, Steven; TAGGI, Andrew, Edmund; BEREZNAK, James, Francis; WO2012/31061; (2012); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 1194-65-6 as follows. Quality Control of 2,6-Dichlorobenzonitrile

In the same manner as in the process of the fluorination step of Example 1 except for using 17.2 g of 2,6-dichlorobenzonitrile instead of 2,3,6-trichlorobenzonitrile, the reaction and refinement were carried out to obtain 9.5 g of 2,6-difluorobenzonitrile (yield: 68%).

According to the analysis of related databases, 1194-65-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US4406841; (1983); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 96606-37-0,Some common heterocyclic compound, 96606-37-0, name is 2,4,6-Trifluorobenzonitrile, molecular formula is C7H2F3N, 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.

In one embodiment,The 6 mmol of the second reactant was dissolved in 15 ml to 25 ml of the first solvent tetrahydrofuran, and then 0.5 mmol to 2 mmol of the first additive sodium hydride was slowly added.The reaction is carried out for 20-50 minutes under room temperature conditions and under nitrogen.Then 2 second of the first reactant was added to continue the reaction for 12 hours.A mixture comprising the electroluminescent material is obtained.The mixture of the electroluminescent material is cooled to room temperature and poured into distilled water.Extraction with a second extraction solvent, and then washing with a second detergent,Drying with a second desiccant, and then performing chromatography,Obtaining a second crude product, and then eluting with a second eluent to obtain the electroluminescent material, wherein the electroluminescent material is a white solid,The yield was 54%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4,6-Trifluorobenzonitrile, its application will become more common.

Reference:
Patent; Wuhan Hua Xing Optoelectric Semiconductor Display Co., Ltd.; Jing Xiaofang; (40 pag.)CN110229094; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 654-70-6, The chemical industry reduces the impact on the environment during synthesis 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, I believe this compound will play a more active role in future production and life.

A. 4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-2-trifluoromethyl-benzonitrile (471A) A mixture of 3-trifluoromethyl-4-cyano-aniline (24.0 g, 129 mmol) and maleic anhydride (14.0 g, 143 mmol) in 50 mL of acetic acid was heated at 115 C. overnight. A precipitate was obtained during the heating period. The reaction was allowed to stand at rt for an additional overnight period. The solid was removed by filtration, the filter cake was washed with diethyl ether and dried to give 21 g (79 mmol, 61%) of compound 471A as an off white solid. HPLC: 100% at 2.11 min (retention time) (YMC S5 ODS column, 4.6*50 mm, eluding with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

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, 4-Cyano-3-trifluoromethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Salvati, Mark E.; Balog, James Aaron; Pickering, Dacia A.; Giese, Soren; Fura, Aberra; Li, Wenying; Patel, Ramesh N.; Hanson, Ronald L.; Mitt, Toomas; Roberge, Jacques Y.; Corte, James R.; Spergel, Steven H.; Rampulla, Richard A.; Misra, Raj N.; Xiao, Hai-Yun; US2004/77605; (2004); A1;,
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. 123-06-8, name is Ethoxymethylenemalononitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethoxymethylenemalononitrile

To 2-(ethoxymethylene)propanedinitrile (20 g, 163.80 mmol) was added hydrazine hydrate (15.9 mL, 327.60 mmol) dropwise at 0 C and the resultant reaction mixture was heated at 100 C in a closed reagent bottle for 1 h. The reaction was monitored by TLC. After completion of reaction, the mixture was cooled to RT and water (50 mL) was added to the reaction mixture. The product was extracted using EtOAc (3×200 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 15 g of 5-amino-1H-pyrazole-4-carbonitrile as a light brown solid.

The synthetic route of 123-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; GREEN, Michael, John; PHAM, Son, Minh; PUJALA, Brahmam; AGARWAL, Anil, Kumar; NAYAK, Ajan, Kumar; KHARE, Sweta; GUGULOTH, Rambabu; RANDIVE, Nitin, Atmaram; WO2015/58084; (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. 19472-74-3, name is 2-Bromophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6BrN

2-Bromophenylacetonitrile (20.0 g, 0.1 mol) was dissolved in THF (100 mL), iced water,1 M borane tetrahydrofuran solution (200 mL, 0.2 mol) was added dropwise, and the mixture was dropped.Slowly warm to 80 C, stir for 24 h, place the cooled ice bath after cooling.Methanol (50 mL), 3N hydrochloric acid (30 mL) were slowly added dropwise, and the temperature was raised to 80 C.Stir for 4 h, concentrate and dilute with water (100 mL) and wash with diethyl ether (50 mL×2).The aqueous phase is adjusted to pH=10 with saturated sodium carbonate solution.Extracted with EA (50 mL×2), dried and concentrated.17.4 g (85.2%) of a pale yellow oily liquid was obtained.

According to the analysis of related databases, 19472-74-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Liu Zhanzhu; Shen Zhufang; Sun Zhaozhu; Pan Xuan; Zhou Tian; Huan Yi; Guan Baohe; (76 pag.)CN110294744; (2019); A;,
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. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H7NO

EXAMPLE 34 This example illustrates the preparation of compound 34. 4-Hydroxymethyl-benzonitrile (3.1 g, 23.3 mmoles) was combined with N,N-diisopropylethylamine (4.9 mL, 28 mmoles) in 100 mL of anhydrous THF. To this solution was added MOMCl (3.5 mL, 46.1 mmoles) and the mixture was stirred at room temperature for 16 hours. After this period a solution of NH4OH/H2O (1:1, 20 mL) was added (-MOMCl) and the solution was stirred for 15 minutes. After this period the reaction mixture was evaporated in vacuo (-THF) and the resulting mixture was extracted with DCM (3*30 mL). The combined DCM layer was dried over anhydrous Na2SO4, evaporated in vacuo, and the resulting crude product was purified using flash silica chromatography (0-20% EtOAc/Hexane) to yield 1.6 g (39% yield) of 4-Methoxymethoxymethylbenzonitrile as a colorless liquid.

According to the analysis of related databases, 874-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayne, Christopher D.; Johnson, Alan T.; Lu, Shao-Po; Mohan, Raju; Griffith, Ronald C.; US2003/181420; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 94087-40-8, name is 3-Chloro-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 94087-40-8, name: 3-Chloro-2-fluorobenzonitrile

To a solution of 11 (3.57 g, 16.9 mmol, 1 eq) and 3-chloro-2-fluorobenzonitrile (5.25 g, 33.74 mol, 2 eq) in dry DMSO (125 mL) was added K2CO3 (7 g, 50.6 mmol, 3.1 eq). The reaction mixture was stirred at rt for 24 h and partitioned between EtOAc and brine. The aqueous phase was extracted with EtOAc and the combined EtOAc extracts were washed with brine, dried over Na2SO4, and evaporated. Chromatography on a silica column with eluent of 20:1 CH2Cl2:Me0H afforded (R)-3-chloro-2-[2-chloro-5-(5-oxo-pyrrolidin-3-yl> phenoxy]-benzonitrile, 12. 2.4 Results[0172] Analytical data for structure 9 is provided below.2.4a (R)-3-chloro-2-[2-chloro-5-(5-oxo-pyrrolidin-3-yl)’phenoxy]-benzonit}”ile [0173] MS m/z 347.0 (M + 1).

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; IRM LLC; WO2006/81554; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts