Tag: M.W=200-300

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;,
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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. 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, A new synthetic method of this compound is introduced below., name: 2-Bromo-4-chlorobenzonitrile

[0911] To a solution of 100 g (654 mmol) of (2-methoxy- pyridin-4-yl)boronic acid and 142 g (654 mmol, 1 eq.) of 2-bromo-4-chlorobenzonitrile in 2.01 of dioxane were added981 ml (1961 mmol, 3 eq.) of 2 N aqueous sodium carbonate solution. Argon was passed through the reaction mixture for 10mm, 53mg (65 mmol, 0.1 eq.) of[1,1-bis(diphenylphos- phino)ferrocene] dichloropalladium dichioromethane complex were added and the mixture was stirred at 85 C. for 6 h. The mixture was then stirred at RT overnight. The reaction mixture was admixed with 3 1 of water and 1 1 of methyl tert-butyl ether, filtered through kieselguhr and washed through with 11 of methyl tert-butyl ether. The filtrate was separated and the aqueous phase was extracted twice with 1 1 of methyl tert-butyl ethet The combined organic phases were dried over sodium sulphate and concentrated. The filtercake was washed three times with 800 ml of dichloromethane and the organic phase was dried over sodium sulphate and concentrated. Subsequently, the two residues were combined and stirred in methanol. The precipitate was filtered oil with suction and washed twice with methanol. The filtrate was concentrated and dissolved together with the precipitate in dichloromethane. Subsequently, activated carbon was added and the mixture was stirred under reflux for 30 mm. The reaction mixture was subjected to hot filtration through kieselguhr, and the filtrate was concentrated. The residue was stirred again in methanol, and the precipitate was filtered off with suction and washed twice with methanol. The filtrate was concentrated, and the precipitate was filtered off with suction and washed with methanol. The two precipitates were combined and dried under high vacuum overnight. The filtrate was concentrated and purified by means of flash chromatography (eluent: dichloromethane/ methanol, 0-2%). The product fractions were combined, concentrated and stirred in warm methanol. The precipitate was filtered off with suction, washed with methanol and dried under high vacuum. Overall yield: 120 g (75% of theory).10912] LC/MS [Method 1]: R=1.02 mm; MS (ESIpos):mlz=245 (M+H), j0913] ?H-NMR (400 MHz, DMSO-d5): oe [ppm]=8.33 (d, 1H), 8.04 (d, 1H), 7.82 (d, 1H), 7.76 (dd, 1H), 7.22 (dd, 1H),7.07 (s, 1H), 3.92 (s, 3H).

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; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; JIMENEZ-NUNEZ, Eloisa; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; ACKERSTAFF, Jens; STAMPFUss, Jan; (87 pag.)US2017/291892; (2017); A1;,
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Reference of 6575-05-9,Some common heterocyclic compound, 6575-05-9, name is 2,4,6-Trichlorobenzonitrile, molecular formula is C7H2Cl3N, 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 57; N-{[1-{[4-(1,1-Dimethylethyl)phenyl]methyl}-4-hydroxy-6-oxo-2-(2,4,6-trichlorophenyl)-1,6-dihydro-5-pyrimidinyl]carbonyl}glycine; 57a) 3-{[4-(1,1-Dimethylethyl)phenyl]methyl}-6-hydroxy-2-(2,4,6-trichlorophenyl)-4(3H)-pyrimidinone; A 1 M solution of dimethylaluminium chloride in hexane (2.75 mL, 2.75 mmol) was added to a stirred mixture of 4-tert-butylbenzylamine (0.408 g, 2.50 mmol), 2,4,6-trichlorobenzonitrile (0.619 g, 3.00 mmol) and toluene (3 mL) at room temperature. After 2 min at room temperature, the mixture was stirred in a microwave reactor at 150 C. for 0.5 h, then cooled and the solvent removed under reduced pressure. Diethyl malonate (1.60 g, 10.0 mmol), 2-methoxyethanol (15 mL) and 4.37 M sodium methoxide in methanol (2.30 mL, 10.0 mmol) were added and the mixture refluxed under nitrogen for 8 h. After cooling, the mixture was poured into water (150 mL), washed with ether, acidified to pH 1 with 6 M aqueous hydrochloric acid, and extracted with ethyl acetate. The extracts were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with ether and the solid collected, washed with ether and dried to give the title compound (0.551 g, 50%) as a solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.23 (s, 9 H) 4.88 (s, 2 H) 5.59 (s, 1 H) 6.79-6.85 (m, 2 H) 7.18-7.25 (m, 2 H) 7.84 (s, 2 H) 11.94 (br. s., 1 H).

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-Trichlorobenzonitrile, its application will become more common.

Reference:
Patent; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); 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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C8F4N2

Example 1; Synthesis of hexadecafluorovanadylphthalocyanine; Into a separable flask of glass provided with a stirrer, a thermometer, a water separation tube, and a cooling tube and having an inner volume of 300 ml, a nitrogen gas was introduced at a rate of 500 ml/min for 10 minutes to replace the interior of the reaction vessel with the nitrogen gas. Then, the reaction vessel was charged with 30 gr (0.15 mol) of tetrafluorophthalonitrile, 58.6 gr (0.45 mol) of n-octanol, and 6.9 gr (0.0438 mol) of vanadium trichloride (produced by Sinko Kagaku K.K.). Again, a nitrogen gas was introduced at a rate of 500 ml/min for 10 minutes into the reaction vessel to replace the interior thereof with the nitrogen gas. When the oxygen concentration in the reaction vessel was determined with an oxygen concentration meter, it was found to be 1.8 vol percent. Under the condition of continued stirring, the reaction mixture in the reaction vessel was exposed to a current of nitrogen gas at a flow rate of 30 ml/min and heated. The linear speed of the gas at the inlet part (the connecting part between the reaction vessel and the cooling tube) was 0.6 cm/sec and the oxygen concentration in the reaction vessel was measured with an oxygen concentration meter to be found to be 1.8 vol percent. The temperature was elevated to 150¡ã C. over two hours, then the reaction was further continued for three hours, and the reaction vessel was left cooling to normal room temperature. In the meanwhile, the flow of the nitrogen gas was continued. The conversion of tetrafluorophthalonitrile was determined by liquid chromatography, to find to be 99.2percent. The slurry resulting from the cyclization was filtered to separate a solid component. The solid component was washed with 300 gr of benzonitrile, then washed with 100 gr of methanol, and dried under a reduced pressure at 150¡ã C. for 12 hours. The weight of the target product, hexadecafluorovanadyphthalocyanine, as calculated from the weight after drying, was 28.1 gr (yield: 86.4 mol percent).; Comparative Example 4; When the reaction was performed by following the procedure of Example 1 while omitting the replacement with a nitrogen gas prior to the reaction and the introduction of a nitrogen gas during the course of the reaction, and supplying air at a flow rate of 30 ml/min to the reaction vessel, the weight of hexadecafluorovanadyl phthalocyanine was found to be 12.5 gr (yield: 38.5 mol percent). When the oxygen concentration in the reaction vessel was determined at this time with an oxygen concentration meter, it was found to be 20.3 vol percent.

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; Hirota, Kouichi; Hashimoto, Yukihide; Masuda, Kiyoshi; Kitao, Masunori; US2005/203293; (2005); A1;,
Nitrile – Wikipedia,
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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;,
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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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Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-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 36282-26-5, COA of Formula: C7H3BrFN

Sodium Hydride (60% oil suspension, 20 mmol, 800 mg) is triturated with hexane and suspended in N,N-dimethylformamide (10 mL). 3-Acetylindole (10 mmol, 1.59 g) is added to the ice-cooled suspension. After 5 minutes, 2-bromo, 4-fluorobenzonitrile (14 mmol, 2.8 g) is added. The reaction is stirred at 50 degrees Celsius for 30 minutes. The reaction mixture is allowed to cool and is extracted into ethyl acetate (200 mL) and is washed with water (50 mL). The organic phase is dried over magnesium sulfate. Filtration, followed by concentration, and silica gel chromatography affords the desired 4-(3-Acetyl-indol-1-yl)-2-bromo-benzonitrile as a tan solid (0.92 g, 36%)

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; Serenex, Inc.; US2007/185184; (2007); A1;,
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Synthetic Route of 185836-35-5,Some common heterocyclic compound, 185836-35-5, name is 4-(Benzyloxy)-2-fluorobenzonitrile, molecular formula is C14H10FNO, 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.

16.1. 6-(Phenylmethoxy)-1,2-benzisothiazol-3-amine A mixture of 13.2 g (0.058 mol) of 2-fluoro-4-(phenylmethoxy)benzonitrile and 1.85 g (0.058 mol) of sulphur in 15 ml (0.58 mol) of ammonia and 50 ml of methylglycol is brought to 100 C. in an autoclave over 5 hours. The methylglycol is subsequently evaporated off under reduced pressure. The mixture is taken up in dichloromethane, the insoluble material is filtered off, and then the solvent is evaporated off under reduced pressure. The product is purified by chromatography on a silica column with cyclohexane and ethyl acetate in proportions of 60:40. Subsequently, a second purification by chromatography on a silica column with a mixture of diisopropyl ether and methanol in proportions of 99:1 leads to 1.7 g of product. Melting point: 158 C.

The synthetic route of 185836-35-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Synthelabo; US5843975; (1998); A;,
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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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8F4N2

SYNTHESIS EXAMPLE 2 Synthesis of 3-(2,6-dibromo-4-methylphenoxy)-4,5-bis(2,5-dichlorophenoxy)-6-fluorophthalonitrile In a four-neck separable flask having an inner volume of 500 ml, 60 g (0.30 mol) of tetrafluorophthalonitrile, 41.8 g (0.72 mol) of potassium fluoride, and 160 ml of acetone were placed. Further, in a dropping funnel attached thereto, 97.8 g (0.60 mol) of 2,5-dichlorophenol and 110 ml of acetone were placed. The 2,5-dichlorophenol/acetone mixed solution was added dropwise from the dropping funnel to the flask over a period of about two hours while kept stirred at -1¡ã C. The stirring was subsequently continued for about two hours. Thereafter, the contents of the flask were stirred overnight, with the reaction temperature thereof slowly raised to room temperature. Then, to this flask, 79.8 g (0.30 mol) of 2,6-dibromo-4-methylphenol, 20.9 g (0.36 mol) of potassium fluoride, and 15.0 ml of acetone were charged and the mixture was kept stirred at 40¡ã C. for 10 hours. The reaction solution was cooled and filtered. The filtrate was distilled by a rotary evaporator to expel the acetone and was recrystallized from methanol. The produced crystals were separated by filtration and vacuum dried to afford 176.8 g of 3-(2,6-dibromo-4-methylphenoxy)-4,5-bis(2,5-dichlorophenoxy)-6-fluorophthalonitrile (yield: 80.5 mol percent).

The synthetic route of 1835-65-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Shobukai Co., Ltd.; US6323340; (2001); B1;,
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Synthetic Route of 1953-99-7, 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. 1953-99-7 name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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.

Five grams of 3,4,5,6-tetrachlorophthalonitrile, 3.25 grams of 2-bromophenol, 3.9 grams of K2CO3, and 25 milliliters of N, N-dimethylformamide were placed in a 100 milliliter flask , Followed by stirring while heating at 70 ¡ãC. EIA (ethyl acetate) was used for extraction when the reaction was completed. After extraction, the resultant was concentrated to obtain a solid. In this context, the solid obtained is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried in vacuo to give 3,4,6-dichloro-5- (2-bromo-phenoxy ) -phthalonitrile.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Sanxing SDI Co., Ltd.; Zheng Yishu; Xu Huiyuan; Xin Mingye; Shen Xianxiong; Zheng Zhouhao; Han Guishi; (48 pag.)CN107522704; (2017); A;,
Nitrile – Wikipedia,
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