Month: June 2021

Synthetic Route 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.

(Methylsulfinyl) (methylthio) methane (7.26g, 0.0584 mol) was dissolved in 100 mL of dry THF under argon and was cooled [TO-78C.] Butyllithium in hexane (16 mL 1. 6M, 0.0256 mol) was added dropwise with stirring. The mixture was stirred for 15 min. Meanwhile, a solution of 3,4, 5-trifluorobenzonitrile (4.0 g, 0.025 mmol) in 100 [ML] of dry THF was cooled to-78C under argon and the former solution was added through a cannula to the latter solution over a period of 35 min. After 30 min, the cooling bath was removed and when the reaction had reached room temperature it was poured into 400 mL of water. The THF was evaporated and the remaining aqueous layer was extracted three times with diethyl ether. The combined ether phase was washed with water, dried [(NA2SO4)] and evaporated. Yield: 2.0 g (30%). ‘H NMR (500 MHz, [CDC13)] 8 7.4-7. 25 (m, 2H), 5.01 (s, [1H,] diasteromer), 4.91 (s, [1H,] diasteromer), 2.88 (s, 3H, diasteromer), 2.52 (s, 3H, diasteromer), 2.49 (s, 3H, diasteromer), 2.34 (s, 3H, diasteromer), 1.72 (broad, [1H)]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5-Trifluorobenzonitrile, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2003/101956; (2003); A1;,
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Reference of 906673-45-8,Some common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, molecular formula is C14H10BrNO2, 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.

40.0 g (131 mmol) of 4-(4-bromo-3-hydroxymethyl-phenoxy)-benzonitrile of formula (II), prepared as described in Example 3, are added under nitrogen to 400 mL THF and 23.8 g (236 mmol) of triethylamine in a previously anhydrified flask. The solution is cooled down to 0 C. and 16.9 g (157 mmol) of trimethylsilyl chloride are added maintaining the temperature below 15 C. After completion of the addition, the mixture is allowed to reach room temperature. 50 mL of toluene and 100 mL of water are added and the phases are separated. The organic phase is washed with a saturated NaCl solution and evaporated to dryness under reduced pressure to obtain 49.4 g of 4-(4-bromo-3-trimethylsilanoxymethyl)-benzonitrile of formula (II) as a solid with a yield of 98%. The obtained product is used in the next step any without further purification. 1H-NMR (CDCl3, 300 MHz) delta (ppm): 7.63-7.60 (2H, m) 7.52 (1H, d, J=8.4 Hz), 7.22 (1H, m) 7.03-7.00 (2H), 6.85-6.80 (1H, m) 4.69 (2H, s), 0.17 (9H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, its application will become more common.

Reference:
Patent; DIPHARMA FRANCIS S.R.L.; Santillo, Niccolo’; Attolino, Emanuele; Brenna, Davide; Vladiskovic, Chiara; Lombardo, Alessandro; Razzetti, Gabriele; US2019/241585; (2019); A1;,
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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;,
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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. 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;,
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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;,
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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 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;,
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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;,
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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;,
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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. 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;,
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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. 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;,
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