Category: nitriles-buliding-blocks

Application of 89642-49-9, These common heterocyclic compound, 89642-49-9, name is 4-Bromo-3-nitrobenzonitrile, 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.

15.18 g (52.85 mmol) of 9-phenyl-9H-carbazole-3-yl-boronic acid, 10 g (44.04 mmol) of 4-bromo-3-nitrobenzonitrile, and 0.05 percent by weight (wt %) of a palladium catalyst were dissolved in 25 ml of toluene, 25 ml of 2 molar (M) potassium carbonate was added thereto, and the resulting reaction solution was stirred for 24 hours. After completing the reaction, the resulting reaction solution was extracted using chloroform to remove a solvent therefrom. Then, the resulting solid product was dried. 3 equivalents of triphenylphosphine were added thereto, and the mixture was stirred in dichlorobenzene for 12 hours at a temperature of 160 C. After completing the reaction, 100 ml of methanol was slowly added to the mixture, to thereby filter the resulting reaction solution. The filtered crude product obtained therefrom was dried and purified by column chromatography with a mixture of dichloromethane and hexane as an eluent, thereby obtaining 4.87 g (yield: 31%) of Intermediate 4. The structure of the synthesized compound was identified using a MALDI-TOF mass spectrometer. (0347) MALDI-TOF (calculated: 357.1 g/mol, measured: [M+H]+=358 g/mol)

Statistics shows that 4-Bromo-3-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 89642-49-9.

Reference:
Patent; SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.; Jeon, Soonok; Numata, Masaki; Lee, Saeyoun; Miyazaki, Hiroshi; Son, Jhunmo; Sim, Myungsun; Lee, Namheon; Ihn, Sooghang; (116 pag.)US10510966; (2019); B2;,
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Related Products of 160892-07-9, 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. 160892-07-9 name is 5-Bromoisophthalonitrile, 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.

5-bromoisophthalonitrile (1 g, 48.3 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolo[3,2,1-jk]carbazole (1.77 g, 48.3 mmol) were dissolved in 1,4dioxane (50 ml). K2CO3 (1.34 g, 96.6 mmol) was dissolved in water and poured into the mixture. The reaction mixture was stirred with N2 bubbling for 30 min and refluxed overnight. After cooling to room temperature, the mixture was filtered and diluted with methylene chloride and washed with distilled water. The organic layer was dried over anhydrous MgSO4 and evaporated in vacuum. And then, the product was isolated by column chromatography on a silica gel.

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

Reference:
Patent; RESEARCH & BUSINESS FOUNDATION SUNGKYUNKWAN UNIVERSITY; LEE, Junyeob; IM, Yirang; (37 pag.)US2018/114924; (2018); A1;,
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Application of 4435-14-7, 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. 4435-14-7, name is 2-Cyclohexylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 0.846 g (8.1 mmol) of hydroxylamine hydrochloride in 1 1 mL of isopropyl alcohol, 1 .499 g (17.8 mmol) of sodium bicarbonate was added. The resulting mixture was stirred at 25 C to 30 C for 10 – 15 min. 1 .0 g (8.1 mmol) of 2- cyclohexylacetonitrile was added and stirred at 80 C to 85 C for 3 – 4 h. After completion of the reaction, the reaction mixture was cooled to 25 C to 30 C, filtered and washed with 2 mL of isopropyl alcohol. The filtrate was collected and distilled out completely to obtain a crude residue. The residue was chased with 5 mL of toluene to yield the title compound.Yield: 0.6 g (47 %).

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-Cyclohexylacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PIRAMAL LIFE SCIENCES LIMITED; SIVAKUMAR, Meenakshi; JOSHI, Kalpana Sanjay; AWARE, Valmik Sopan; SARDE, Ankush Gangaram; BAGUL, Sandeep Mukunda; MANOHAR, Sonal Mohan; WO2011/104680; (2011); A1;,
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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. 41963-20-6, name is 4-Bromo-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6BrN

Step F tert-Butyl 4-(4-cyano-2-methylphenyl)-3,6-dihydropyridine-1(2H)-carboxylate. A mixture of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (0.40 g, 0.0013 mol), 4-bromo-3-methylbenzonitrile (0.30 g, 0.0016 mol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1, 0.063 g, 0.000078 mol) and potassium carbonate (0.54 g, 0.0039 mol) in N,N-dimethylformamide (6.0 mL, 0.077 mol) was stirred under nitrogen at 80 C. overnight. The mixture was diluted with ethyl acetate, washed with water and brine successively, dried and concentrated. The product was purified by CombiFlash using hexane/EtoAc (max. EA 30%) LC-MS: 299.2 (M+H)+

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 41963-20-6.

Reference:
Patent; Burns, David M.; Yao, Wenqing; He, Chunhong; US2005/250789; (2005); A1;,
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These common heterocyclic compound, 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, 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. category: nitriles-buliding-blocks

10% Palladium on carbon (5.06 g) was added under an atmosphere of nitrogen to a chilled (ice- water bath) solution of 2-(3 -methyl- IH-1, 2,4- triazol-l-yl)-5-nitrobertzonitrile (10.9 g, 47.6 mmol) dissolved in methanol (100 mL). The flask was repeated evacuated and flushed with hydrogen gas (double balloon). The resulting mixture was allowed to warm to rt and left to stir for 16 h under the hydrogen atmosphere. Purged with nitrogen gas. Filtered the crude reaction mixture through a short dialomaceous earth (Celite ) plug. Rinsed reaction vessel and plug with methanol. Concentrated filtrate in vacuo. Dried residue on high vacuum overnight to afford 5-amino-2-(3-methyl-lH-l,2,4-triazol-l-yI)benzonitrile (6.59 g, 70 % yield) as a brown solid. LC-MS (M+H)+ 200.0. 1H NMR (500 MHz, DMSO- J6) delta ppm 2.29 – 2.37 (m} 3 H) 5.99 (s, 2 H) 6.94 (dd, J=8.85, 2.44 Hz, 1 H) 7.00 (d, J-2.44 Hz, 1 H) 7.37 (d, J=8.54 Hz, 1 H) 8.69 – 8.81 (m, 1 H).

The synthetic route of 2-Chloro-5-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
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Application of 501-00-8, 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 501-00-8 as follows.

Step 1: 2-(3-fluoro-phenyl)-2-methyl-propionitrile Under an argon atmosphere 77 mL (77 mmol) of a 1M lithium bis(trimethylsilyl)amide solution was added dropwise at -70 C. to 5.0 g (37 mmol) (3-fluoro-phenyl)-acetonitrile in 150 mL THF. The mixture was allowed to come up to -50 C. and was then stirred at this temperature for 1 h. Then at -50 C. 4.8 mL (78 mmol) methyl iodide were added. The reaction mixture was heated to RT overnight. The reaction mixture was slowly combined with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried on sodium sulphate and evaporated down. Yield: 5.6 g (93% of theory) ESI-MS: m/z=163 (M+H)+

According to the analysis of related databases, 501-00-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
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Synthetic Route of 50846-36-1, A common heterocyclic compound, 50846-36-1, name is 2-Amino-2-methylpropanenitrile hydrochloride, molecular formula is C4H9ClN2, 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.

Triethylamine (93 mL, 683 mmol, 3 equiv) was added to a solution of compound 32 (46 g, 228 mmol, 1 equiv) and HBTU (99 g, 262 mmol, 1.15 equiv) in DMF (690 mL). After stirring at room temperature for 30 minutes, 2-amino-2-methylpropanenitrile hydrochloride (35.7 g, 296 mmol, 1.3 equiv) was added and the reaction mixture was stirred overnight. The solution was poured into water (4 L) (0512) and extracted with ethyl acetate (3 L). The organic layer was separated, washed with saturated brine (2 L) and concentrated under reduced pressure. The crude product which was dissolved in dichloromethane and purified over silica gel (0.7 Kg), eluting with a gradient of 10 to 20% ethyl acetate in heptanes to give 6-bromo-N-(2-cyanopropan-2-yl)picolinamide.

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; PLEXXIKON INC.; ZHANG, Chao; WU, Guoxian; SPEVAK, Wayne; GUO, Zuojun; ZHANG, Ying; (138 pag.)WO2018/226846; (2018); 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. 145498-86-8, name is Methyl 2-(cyanomethyl)-3-methoxybenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 145498-86-8

Into a 500 mL 3-neck round bottom flask was added 10 g (61.75 mmol) of 2-bromomethyl, 3-methoxy methyl benzoate, 4.0 g (81.6 mmol) of NaCN, 0.30 g (2 mmol) of NaI, 100 mL of CH3CN, and 50 mL of DMF. The reaction mixture was heated and refluxed for 10 hours. The precipitate (NaBr) was filtered off, and the solution was concentrated on an evaporator. 300 mL of water and 200 mL of ether were added and then shaken in a separatory funnel. The water was extracted twice with 100 mL of ether. The ether fractions were dried over MgSO4, and concentrated to yield methyl 3-methoxy-2-cyanomethylbenzoate (95-100% yield). This ester (0.053 mmol, 10.51 g) was stirred vigorously in 100 mL of CH3OH. Ba(OH)2 H2O (0.079 mmol, 14.97 g) was added and the mixture stirred at room temperature overnight. The CH3OH was removed on a rotary evaporator. 150 mL of water, 200 mL of CH2Cl2, and 50 mL of 6N HCl were added, and then stirred in a flask to dissolve all residues. The mixture was transferred to a separatory funnel, acidified with 6N HCl to pH 1-2. The CH2Cl2 phase was separated and the aqueous phase extracted twice with 50 mL of CH2Cl2. The CH2Cl2 extracts were combined, dried over MgSO4 and charcoal, filtered, and evaporated to yield 8.8 g of a white solid, 2-cyanomethyl-3-methoxybenzoic acid, (87%). Methyl 3-methoxy-2-cyanomethylbenzoate: 1H NMR (CDCl3, 300 MHz) delta (ppm): 7.6 (d, 1H), 7.4 (t, 1H), 7.1 (d, 1H), 4.18 (s, 2H), 3.94 (s, 3H), 3.926 (s, 3H). TLC (1:1 ethyl acetate: hexane) 0.55. 2-Cyanomethyl-3-methoxybenzoic acid: 1H NMR (300 Mhz, CDCl3) delta (ppm): 7.55 (d, 1H), 7.45 (t, 1H), 7.3 (d, 1H), 4.121 (d, 2H), 3.91, (s, 3H). TLC (1:1 ethyl acetate: hexane

The synthetic route of 145498-86-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hormann, Robert Eugene; Potter, David W.; Chortyk, Orestes; Tice, Colin M.; Carlson, Glenn Richard; Meyer, Andrew; Opie, Thomas R.; US2006/20146; (2006); A1;,
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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. 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-3-fluorophenylacetonitrile

General procedure: To a 5 mL Schlenk tube were added aryl / heteroaryl acetonitriles 1 (1.0 mmol, 1.0 equiv.), vinyl diphenylsulfonium triflate (434.4 mg, 1.2 mmol, 1.2 equiv.), and DMSO (5 mL). The mixture was stirred at room temperature for 2 min and to the mixture DBU (456 mg, 3 mmol, 3.0 equiv.) was added. The mixture was stirred for 12 hours at room temperature, and then to the mixture was added saturated ammonium chloride solution (25 mL). The resulting mixture was extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with H2O (2 x 30 mL), dried with anhydrous sodium sulfate. After concentration, product 2 was purified using silica gel column chromatography using an appropriate eluent.

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 499983-13-0.

Reference:
Article; Zhou, Mingwei; Hu, Yimin; En, Ke; Tan, Xuefei; Shen, Hong C.; Qian, Xuhong; Tetrahedron Letters; vol. 59; 14; (2018); p. 1443 – 1445;,
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Reference of 4553-07-5, The chemical industry reduces the impact on the environment during synthesis 4553-07-5, name is Ethyl 2-cyano-2-phenylacetate, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of methyleneindolinone (0.1 mmol, 1 equiv), and isocyanide (0.15 mmol, 1.5 equiv) in toluene (0.2 mL) was added catalyst VI (0.005 mmol, 0.05 equiv). The resulting mixture was stirred at room temperature (23C). After the reaction completed, the mixture was quenched with water (5 mL) and extracted with ethyl acetate (2 x 5 mL). The combined organic layer was washed with brine and dried over Na2SO4. The solvent was then removed under reduced pressure. The product was afforded by silica gel flash chromatography using gradient elution (EtOAc/Hexane = 1:10 to 1:6).

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, Ethyl 2-cyano-2-phenylacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tan, Bin; Zhang, Xuan; Zhong, Guofu; ARKIVOC; vol. 2014; 3; (2014); p. 124 – 142;,
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