Month: August 2021

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. 50594-78-0, name is 5-Fluoro-2-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 50594-78-0

5-Fluoro-2-nitrobenzenecarbonitrile (1.02 equivalents) and N- methylpiperazine (1.0 equivalents) were dissolved in NMP. Triethylamine (2.1 equivalents) was added, and the resulting solution heated at 100 C for 1 hour. The solution was cooled to room temperature and poured into H20. A precipitate formed which was filtered to yield the desired product as a green solid. LC/MS M/Z 247.3 (MH+), Rt 1.46 minutes.

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; CHIRON CORPORATION; WO2004/18419; (2004); A2;,
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Electric Literature of 499983-13-0, 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 499983-13-0 as follows.

EXAMPLE 2Cyclopropanation of 4-bromo-3-fluorophenylacetonitrile (II) with ethylene sulfate (III) to give 4-bromo-3-fluorophenyl-cyclopropanenitrile (IV)24 ml of lithium bis(trimethylsilyl)amide (1M in THF, 24 mmol, 2.2 eq.) were loaded at T=-20 C in a 50 ml dried reactor under nitrogen. 2.34 g of 4-bromo-3-fluorophenylacetonitrile (10.92 mmol, 1.0 eq.), dissolved in 5 ml of dry THF, and 1.49 g of ethylene sulfate (12.0 mmol, 1.1 eq.), dissolved in 5 ml of dry THF, were added in the reactor. The mixture was kept under stirring at T=-20 C. for 4 h and then heated to 20 C. The reaction was quenched by adding NH4Cl (saturated solution) and extracted with toluene. The organic layer was concentrated to dryness at reduced pressure to yield 3.01 g of crude product (assay=69.4%; molar yield=79.7%).

According to the analysis of related databases, 499983-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIESI FARMACEUTICI S.p.A; VERZINI, Massimo; Cotarca, Livius; Guidi, Alberto; Melloni, Alfonso; Maragni, Paolo; US2014/378696; (2014); A1;,
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Electric Literature of 77326-36-4, These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, 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.

To a solution of 2-ethoxy-N-(trans-4-hydroxycyclohexyl)acetamide (20.10 g, 99.87 mmol) in anhydrous 1,4-dioxane (800 mL), was added portion-wise sodium hydride (4.33 g, 108.25 mmol, 60% in mineral oil) at room temperature under nitrogen. The mixture was stirred for 1 h at room temperature, and then a solution of 2-amino-6-fluorobenzonitrile (11.34 g, 83.30 mmol) in anhydrous 1,4-dioxane (200 mL) was added drop-wise. The reaction mixture was heated at 90 oC over 72 h, cooled to room temperature, concentrated under reduced pressure, ice water (150 mL) was carefully added and extracted with EtOAc (5 x 200 mL). The combined extract was washed with brine, dried over MgSO4, filtered and the solvent was evaporated. The residue was purified by silica gel column chromatography (35% to 65% EtOAc in hexanes) to afford 18.98 g (72%) of the title compound as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 7.18 (t, J = 8.2 Hz, 1H), 6.44 (d, J = 8.2 Hz, 1H), 6.29 (d, J = 8.3 Hz, 1H), 6.21 (d, J = 8.3 Hz, 1H), 4.39 (br s, 2H), 4.31-4.21 (m, 1H), 4.91 (s, 2H), 3.97-3.84 (m, 1H), 3.57 (q, J = 7.0 Hz, 2H), 2.19-2.05 (m, 4H), 1.78-1.63 (m, 2H), 1.44-1.29 (m, 2H), 1.24 (t, J = 7.0 Hz, 3H). MS 318 (MH+).

The synthetic route of 77326-36-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SENOMYX, INC.; PETROVIC, Goran; FOTSING, Joseph; SERVANT, Guy; TACHDJIAN, Catherine; KARANEWSKY, Donald; VONG, Binh; BOREN, Brant, Clayton; CHEN, Qing; ZHANG, Hong; CHING, Brett, Weylan; LAPERA, Stephanie; (99 pag.)WO2016/73251; (2016); A1;,
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Reference of 2338-75-2, 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. 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 4-(trifTuoromethyl)phenylacetonitrile (2.0 g, 10.8 mmol) and carbon disulfide (714 muL, 11.8 mmol) in tetrahydrofuran (30 rnL) is added dropwise to a solution of sodium hydride (950 mg, 24 mmol) in tetrahydrofuran (20 mL) at 0 0C and stirred at room temperature for 3h. The mixture is cooled to 0 0C, and methyl iodide (1.5 mL, 24 mmol) is added slowly and stirred at room temperature for 12h. The mixture is poured into water and extracted with dichloromethane (2 x 60 mL). The organic layers are combined, washed with brine, dried (MgSO4), concentrated and the crude material is purified by flash chromatography (hexanes/ethyl acetate gradient) to provide 3,3-bis(methylthio)-2-(4-(trifluoromethyl)phenyl)acrylonitrile N4a. ESIMS calcd. for CI2HHF3NS2 ([M+H]+) 290.0, found 290.1.

The synthetic route of 4-(Trifluoromethyl)phenylacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; ALPER, Phillip; AZIMIOARA, Mihai; COW, Christopher; EPPLE, Robert; LELAIS, Gerald; MECOM, John; MUTNICK, Daniel; NIKULIN, Victor; WO2011/14520; (2011); A2;,
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Application of 2338-75-2,Some common heterocyclic compound, 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, molecular formula is C9H6F3N, 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 mixture of [3-(trifluoromethyl)phenyl]acetonitrile (20.0 g, 108 mmol), O,O-diethyl dithiophosphate (18.2 mL, 119 mmol) and 4M hydrogen chloride-dioxane solution (216 mL, 864 mmol) was stirred at room temperature for 18 hr. To the reaction mixture was added water (200 mL), and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed successively with water (100 mL), 0.2M aqueous sodium hydroxide solution (100 mL) and saturated brine (100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was treated with hexane (200 mL) in an ice bath to allow solidification. The solid was collected by filtration and washed with hexane to give the title compound (21.3 g) as a white solid (yield 90%). 1H NMR (400 MHz, CDCl3) delta 4.17 (2H, s), 6.61 (1H, brs), 7.46 (2H, d, J = 6.8 Hz), 7.52 (1H, brs), 7.67 (2H, d, J = 7.2 Hz).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2530078; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

75279-55-9, name is 2-Chloro-6-fluorophenylacetonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 2-Chloro-6-fluorophenylacetonitrile

N-(2,2-dimethyl-2-(2-chloro-6-fluoro)phenethyl)-N’-(2-thiazolyl)thiourea A solution of 2-chloro-6-fluorophenyl acetonitrile (1.69 g, 10 mmole) in dry THF (70 ml) was cooled to -60 C., and lithium diisopropylamide (5.25 ml, 10.5 mmole) was added. After 30 min, methyl iodide (0.68 ml, 11 ml) was added into the reaction mixture, and the reaction was slowly warmed to 0 C., and kept at 0 C. for 1 hr. Then it was cooled to -60 C. again, and more lithium diisopropylamide (6 ml, 12 mmole) was added. After 30 min, methyl iodide (1.87 ml, 30 mmole) was added. The reaction mixture was allowed to warm to room temperature and kept there for 2 hr after which it was poured into a sodium hydrogen carbonate solution, and extracted with chloroform. The organic phase was washed with water, dried, and the solvent was evaporated in vacuo. The product 2,2-dimethyl-2(2-chloro-6-fluorophenyl)acetonitrile (1.07 g) was isolated by silica gel column chromatography. 1 H-NMR (CDCl3) d: 7.25 (m, 2H, Ph), 7.03 (m, 1H, Ph), 1.98 (s, 3H, Me), 1.96 (s, 3H, Me).

The synthetic route of 75279-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Medivir AB; US5593993; (1997); A;,
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Application of 67832-11-5, These common heterocyclic compound, 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, 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.

Preparation 14: 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)benzonitrile; A mixture of dichloro[1 ,1 ,’-bis(diphenylphosphino)ferrocene] palladium (II) dichloromethane adduct (2.12 g, 2.55 mmol), potassium acetate (7.66 g, 76.5 mmol), and bis(pinacolato) diboron (7.12 g, 28.1 mmol) was flushed with nitrogen. 1 ,2- dimethoxyethane (130 ml_) and 4-bromo-2-methylbenzonitrile (5.00 g, 25.5 mmol) were added. The reaction was stirred at 80C for 5 h. The reaction was cooled to room temperature and filtered through celite. The filtrate was diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried over magnesium sulfate and filtered. Silica gel was added and the mixture was concentrated. The crude material was purified by silica column chromatography eluting with a gradient of 0%- 45% ethyl acetate / heptane to give the title compound (5.07 g, 82%) as a white solid. 1H NMR (500 MHz, DMSO-d6) delta ppm 7.70 (m, 2H), 7.57 (d, 1 H), 2.45 (s, 3H), 1.26 (s, 12H).

Statistics shows that 4-Bromo-2-methylbenzonitrile is playing an increasingly important role. we look forward to future research findings about 67832-11-5.

Reference:
Patent; PFIZER INC.; ARHANCET, Graciela Barbieri; CASIMIRO-GARCIA, Agustin; CHEN, Xiangyang; HEPWORTH, David; MEYERS, Marvin Jay; PIOTROWSKI, David Walter; RAHEJA, Raj Kumar; WO2010/116282; (2010); A1;,
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Related Products of 19472-74-3, 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.

General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60-90 C)-EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60-90C)-EtOAc, 10:1 to 30:1] to give 3am; Yield: 27.9 mg (67%); tan solid; mp 191.3-192.0 C.

The chemical industry reduces the impact on the environment during synthesis 2-Bromophenylacetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
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Synthetic Route of 50594-78-0, 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. 50594-78-0 name is 5-Fluoro-2-nitrobenzonitrile, 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.

Step 1 :To a solution of 2-methoxyethanol (9.6 ml_, 122 mmol) in THF at O0C was added NaH (60% in oil, 4.8 g, 122 mmol). The mixture was stirred at O0C for 15 min. To this solution was added 5-fluoro-2-nitrobenzonitrile (15.0 g, 103 mmol). The solution was then allowed to warm to RT and stirred at ambient temperature for 48 hours. The solution was partitioned between EtOAc and water. The water layer was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified via flash chromatography (SiO2: gradient elution, 100:0 to 10:90 hexanes: EtOAc) to afford the ether (21.7 g, 95%) as a light yellow liquid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Fluoro-2-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2009/5646; (2009); A2;,
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Application of 916792-13-7, 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. 916792-13-7, name is 4-Bromo-2-fluoro-5-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-bromo-2- fluoro-5-methylbenzonitrile (40 g, 190 mmol) in a mixture of sulfuric acid (98 %) and TFA (v/v=4:l, 480 mL) was stirred at 80 0C for 16 h. After the mixture was cooled to room temperature, the resulting mixture was poured into ice-cold water. The resulting precipitate was collected by filtration, washed with water and dried under reduced pressure to give the title compound (41 g, 95 % yield) as a white solid. MS (ESI) m/z 232.0 [M+l]+.

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-Bromo-2-fluoro-5-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; ELSNER, Jan; HARRIS, Roy, L.; LEE, Branden; MORTENSEN, Deborah; PACKARD, Garrick; PAPA, Patrick; PERRIN-NINKOVIC, Sophie; RIGGS, Jennifer; SANKAR, Sabita; SAPIENZA, John; SHEVLIN, Graziella; TEHRANI, Lida; XU, Weiming; ZHAO, Jingjing; PARNES, Jason; MADAKAMUTIL Loui; FULTZ Kimberly; NARLA, Rama K.; WO2010/62571; (2010); A1;,
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