Author: Jessica.F

Synthetic Route of 50397-74-5, The chemical industry reduces the impact on the environment during synthesis 50397-74-5, name is 4-Amino-3-bromobenzonitrile, I believe this compound will play a more active role in future production and life.

Diethyl ethoxymethylenemalonate (8.23 g, 38.1 mmol) was added to a solution of 1 (5.00 g, 25.4 mmol) in 30 mL of toluene. The mixture was then heated to reflux overnight with the condenser open to the air. The resulting solution was cooled down to room temperature and poured into 100 mL of hexanes. The white precipitate was collected and washed with hexanes (3 * 30 mL) to yield 11.9 g of an off-white solid as the desired product. MS ESI (m/z) 367 (M + 1)+; 1H NMR (CDCl3, 300 MHz): delta 11.44 (d, 1H, J = 12.6 Hz), 8.44 (d, 1H, J = 12.9 Hz), 7.86 (d, 1H, J = 1.8 Hz), 7.63 (dd, 1H, J1 = 1.8 Hz, J2 = 8.7 Hz), 7.33 (d, 1H, J = 8.4 Hz), 4.35 (q, 2H, J = 6.9 Hz), 4.27 (q, 2H, J = 6.9 Hz), 1.38 (t, 3H, J = 6.9 Hz), 1.33 (t, 3H, J = 6.9 Hz).

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-Amino-3-bromobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fiorito, Jole; Saeed, Faisal; Zhang, Hong; Staniszewski, Agnieszka; Feng, Yan; Francis, Yitshak I.; Rao, Sudha; Thakkar, Devarshi M.; Deng, Shi-Xian; Landry, Donald W.; Arancio, Ottavio; European Journal of Medicinal Chemistry; vol. 60; (2013); p. 285 – 294;,
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Synthetic Route of 38487-86-4,Some common heterocyclic compound, 38487-86-4, name is 2-Amino-4-chlorobenzonitrile, molecular formula is C7H5ClN2, 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.

2-Amino-4-chlorobenzonitrile(153 mg, 1 mmol), [Cp * IrCl2] 2 (8 mg, 0.01 mmol, 1 mol%),Butyraldehyde oxime (96 mg, 1.1 mmol), p-xylene (2.0 mL) were sequentially added to a 25 mL Schlenk reaction flask.After the mixture was reacted at 70 C for 12 hours, cooled to room temperature, and then added to a 25 mL Schlenk flaskBenzaldehyde (117 mg, 1.1 mmol) was added. The mixture was further reacted at 110 C for 4 hours and then cooled toThe solvent was removed under vacuum at room temperature. Then through several petroleum ether washing, filtration, drying to be pure goalCompound, yield: 91%.

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

Reference:
Patent; Nanjing University of Science and Technology; Zhao Wei; Wang Rongzhou; Li Feng; (17 pag.)CN106478525; (2017); A;,
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42872-74-2, name is 3-Bromo-4-methylbenzonitrile, 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. name: 3-Bromo-4-methylbenzonitrile

[0097] The solution of 3-bromo-4-methylbenzonitrile (3) (2.0 g, 10 mmol), in DMF (12 mL) with Bis(pinacolato)diboron (3.4 g, 13 mmol), and Pd(OAc)2 (0.5 g, 2 mmol), and KOAc (3 g, 30 mmol) was microwaved for 3 h at 80C. The mixture was then diluted with H2O (25 mL) and extracted with EtOAc (2 x 30 mL). [0098] The organic phase was collected and dried over Na2SO4 Column chromatography (in Hexane/Ethyl acetate 9:1) afforded 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (B) as an oil, which solidified during the drying in vacuo (yield: 96%)

The synthetic route of 42872-74-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; CHEN, Shoujun; ZHANG, Junyi; JIANG, Jun; KOWALCZYK-PRZEWLOKA, Teresa; XIA, Zhiqiang; ZHANG, Shijie; WO2013/63385; (2013); 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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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. 326-62-5, name is 2-(2-Fluorophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H6FN

Example 1a Preparation of 2-(2-fluorophenyl)-2-methylpropanenitrile To a 500 mL 3-neck round bottom flask with an attached addition funnel that has been purged with dry N2, was added 2-fluorophenylacetonitrile (11.0 g, 81.4 mmol) and anhydrous THF (70 mL). The reaction solution was cooled to -10 C. prior to dropwise addition of a 1.0 M potassium tert-butoxide solution (195 mL, 2.4 molar equiv) in THF. The reaction solution was stirred at -10 C. for 20 min prior to addition of iodomethane (15.2 mL, 244 mmol). The reaction solution was allowed to stir warming to room temperature for 4 hr. The reaction solution was quenched by addition of aq NH4Cl and diluted with EtOAc (200 mL). The organic phase was partitioned, washed with aq NH4Cl, dried over Na2SO4, filtered, concentrated in vacuo and chromatographed through a 240 g SiO2 column on the Biotage SP-1 using a solvent gradient of 100% Hx to 50% EtOAc to afford 10.1 g (76% yield) of title product. GCMS m/z=163 [M]+.

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 326-62-5.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; EXELIXIS PATENT COMPANY LLC; Busch, Brett B.; Stevens, JR., William C.; Kick, Ellen K.; Zhang, Haiying; Bollu, Venkataiah; Martin, Richard; Mohan, Raju; US2015/299136; (2015); A1;,
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Electric Literature of 1897-52-5, A common heterocyclic compound, 1897-52-5, name is 2,6-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

Example 156A 2-Fluoro-6-(1H-1,2,4-triazol-1-yl)benzonitrile Under argon, 2,6-difluorobenzonitrile (1.00 g, 7.19 mmol) was dissolved in dimethylsulfoxide (4 mL), and 1,2,4-triazole (0.52 g, 7.48 mmol) and cesium carbonate (2.44 g, 7.48 mmol) were added. The mixture was stirred at 50 C. for 5 h. After cooling to RT, water (20 mL) was added and stirring was continued for 15 min. The precipitate was filtered and washed with water (10 mL). The solid was taken up in dichloromethane/water and extracted with dichloromethane. The combined organic phases were washed with brine, and concentrated in vacuo. Purification via column chromatography (silica gel, cyclohexane/ethyl acetate, Gradient) afforded the title compound (0.25 g, 18% of theory). LC-MS (Method 1B): Rt=0.62 min, MS (ESIPos): m/z=189 [M+H]+

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; Hassfeld, Jorma; KINZEL, Tom; Koebberling, Johannes; CANCHO GRANDE, Yolanda; BEYER, Kristin; Roehrig, Susanne; Koellnberger, Maria; SPERZEL, Michael; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; ELLERMANN, Manuel; US2015/126449; (2015); A1;,
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Reference of 873-32-5,Some common heterocyclic compound, 873-32-5, name is 2-Chlorobenzonitrile, molecular formula is C7H4ClN, 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.

General procedure: Typically, an aryl chloride (2.0 mmol), phenylboronic acid (3.0 mmol), Pd(at)NPad2-1.0 catalyst (5.4 mg, 0.02 mol% Pd), K2CO3 (552.8 mg, 4.0 mmol) and 4.0 mL of i-PrOH/water (1:1) were added into a 25 mL pressure tube under Ar. The reaction mixture was stirred at 100 C for 18 h in an oil bath. After the reaction mixture cooled down to room temperature, the product was isolated by column with silica gel and analyzed by 1H NMR.

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

Reference:
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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. 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. 935-02-4, name is 3-Phenylpropiolonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Phenylpropiolonitrile

General procedure: To a solution of cyanoacetylenes (0.4mmol) with N-tosylimines (0.2 mmol) in toluene (2 mL) was added Ph3P (0.2mmol). The mixture was then stirred at 110 C for 36 h in a reaction flask. Thenthe solvent was removed in vacuo and residue was purified by columnchromatography on silica gel to give the desired annulation product.

The synthetic route of 935-02-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Jinfeng; Zhang, Qi; Ji, Xin; Meng, Ling-Guo; Synlett; vol. 30; 9; (2019); p. 1095 – 1099;,
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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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3ClFN

General procedure: To an ice-cooled solution of 12 (0.200 g, 0.979 mmol) in DMF (2.0 mL) was added NaH (60% in mineral oil, 0.047 g, 1.18 mmol), and the mixture was stirred at 0 C for 30 min. To the mixture was added 4-fluorobenzonitrile (0.237 g, 1.96 mmol), and the mixture was stirred at 0 C for 2 h and room temperature for 18 h. The mixture was acidified with saturated aqueous solution of NH4Cl and extracted twice with EtOAc. The organic layers were combined, washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc). The product was recrystallized from hexane-EtOAc to give 3 (0.131 g, 44%) as white crystals.

The synthetic route of 60702-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yamamoto, Satoshi; Tomita, Naoki; Suzuki, Yuri; Suzaki, Tomohiko; Kaku, Tomohiro; Hara, Takahito; Yamaoka, Masuo; Kanzaki, Naoyuki; Hasuoka, Atsushi; Baba, Atsuo; Ito, Mitsuhiro; Bioorganic and Medicinal Chemistry; vol. 20; 7; (2012); p. 2338 – 2352;,
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