Category: 134604-07-2

Reference of 134604-07-2, A common heterocyclic compound, 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, molecular formula is C7H3BrN2O2, 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.

Description for D422-(2-methylpropyl)-5-nitrobenzonitrile (D42)To a solution of isobutylboronic acid (5.89 g), 2-bromo-5-nitrobenzo nitrile (12.5 g) and Cs2C03 (35.9 g) in toluene (150 mL) and water (5 mL) stirred under nitrogen at room temperature was added solid PdCI2(dppf CH2CI2 adduct (2.248 g) in one charge. The reaction mixture was stirred at 100 C for 16 h. After cooling the reacion, the solvent was removed in vacuo. The residue was purified by column chromatography to give 2-(2-methylpropyl)-5-nitrobenzonitrile (D42) (11 g) as a light yellow oil. deltaEta (CDCI3, 400MHz): 1.00 (6H, d), 2.06 (1 H, m), 2.86 (2H, d), 7.52 (1 H, d), 8.37 (1H, dd), 8.51 (1H, d).

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; GLAXO GROUP LIMITED; LIN, Xichen; REN, Feng; ZHANG, Haibo; WO2011/113309; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 134604-07-2, These common heterocyclic compound, 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, 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 1 2-Cyano-4′-methyl-4-nitrobiphenyl To a solution of p-tolyltrimethyltin (389 mg, 1.525 mmol) in dry toluene (5 mL) under N2 was added 2-bromo-5-nitro-benzonitrile (276 mg, 1.22 mmol) and Pd(PPh3)4 (176 mg; 10 mol %). The reaction was stirred at reflux under N2 for 24 hours and then cooled to room temperature. The mixture was diluted with EtOAc and the solid was removed by filtration through a pad of celite. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on a silica column eluding with Hex/EtOAc (10:1) to afford 214 mg (74%) of the titled compound as a slightly yellow solid. 1 H-NMR: (300 MHz, CDCl3) delta 2.42 (s, 3H), 7.32 (d, 2H), 7.48 (d, 2H), 7.69 (d, 1H), 8.45 (dd, 1H), 8.61 (s, 1H).

Statistics shows that 1-Cyano-2-bromo-5-nitrobenzene is playing an increasingly important role. we look forward to future research findings about 134604-07-2.

Reference:
Patent; Merck & Co., Inc.; US5240928; (1993); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 134604-07-2, 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. 134604-07-2 name is 1-Cyano-2-bromo-5-nitrobenzene, 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.

To a solution of isobutylboronic acid (5.89 g), 2-bromo-5-nitrobenzo nitrile (12.5 g) and Cs2C03 (35.9 g) in toluene (150 mL) and water (5 mL) stirred under nitrogen at room temperature was added solid PdCI2(dppf)- CH2CI2 adduct (2.248 g) in one charge. The reaction mixture was stirred at 100 C for 16 h. After cooling the reacion, the solvent was removed in vacuo. The residue was purified by column chromatography to give 2-(2-methylpropyl)-5-nitrobenzonitrile (D56) (11 g) as a light yellow oil. 5H (CDCI3, 400MHz): 1.00 (6H, d), 2.06 (1 H, m), 2.86 (2H, d), 7.52 (1 H, d), 8.37 (1 H, dd), 8.51 (1 H, d).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Cyano-2-bromo-5-nitrobenzene, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; DENG, Guanghui; LIN, Xichen; REN, Feng; ZHAO, Baowei; WO2011/134280; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C7H3BrN2O2

[00305] A microwave vial was charged with 1-propyl-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridin-2(1H)-one (0.200 g, 0.6 mmol), 2-bromo-5-nitrobenzonitrile (0.180 g, 0.8 mmol), and dioxan (8 mL) and water (2 mL) and the flask was degassed and flushed with argon. PdCl2(dppf) (0.058 g, 0.1 mmol) was added and the reaction flask was again degassed and flushed with argon. The reaction mixture was then heated to 100C in a microwave for 45 minutes. The reaction was cooled to room temperature and quenched with sat. NaHC03 and extracted with ethyl acetate (3X50 mL). The combined organics were washed with water, brine and dried over MgS04. The solvents were evaporated to dryness and the residue purified by flash chromatography (silica gel, 0-60% ethyl acetates in hexanes) to afford the product as yellow solid (170 mg, 80%). LC/MS: [M+l]+, 350.2; 1H NMR (300 MHz, CDC13): delta 8.60 (d, J=2.4 Hz, IH), 8.47 (t, J=2.4 Hz, IH), 8.44 (d, J=2.4 Hz, IH), 8.15 (s, IH), 7.84-7.82 (m, 2H), 7.70-7.65 (m, IH), 6.71 (d, J=9.9 Hz, IH), 3.98 (t, J=7.5 Hz, 2H), 1.89-1.81 (m, 2H), 1.02 (t, J=6.9 Hz, 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; FGH BIOTECH, INC.; HUFF, Joel; UESUGI, Motonari; KINCAID, John; (213 pag.)WO2017/190086; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 134604-07-2,Some common heterocyclic compound, 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, molecular formula is C7H3BrN2O2, 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 suspension of 2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropa ne-1-carboxamido)benzamide (C340) (600 mg, 1.326 mmol), 2-bromo-5-nitrobenzonitrile (361 mg, 1.591 mmol), cesium carbonate (605 mg, 1.856 mmol), tris(dibenzyideneacetone)dipaladium(0) ( Pd2(dba)s, 36.4 mg, 0.040 mmol), and bis(diphenylphosphino)-9,9-dimethylxa nthene (Xantphos, 69.0 mg, 0.119 mmol) in 1,4- dioxane (8.9 ml.) was evacuated under vacuum and backfilled with nitrogen three times. The reaction mixture was sealed under a blanket of nitrogen and heated to 60 C by microwave irradiation for 2 hours. The reaction mixture was diluted with ethyl acetate and filtered through Celite ” . The solvent was removed via rotary evaporation to give a deep red solid . The solid was suspended in dichloromethane ( 10 mL) and then collected by vacuum filtration, washing with more dichloromethane to afford the title compound as a red solid (0.598 g, 75% ) : N M R (400 MHz, Acetone- e) missing one amide NH in baseline delta 10.26 (s, 1H), 8.73 (d, J = 2.6 Hz, 1H), 8.62 (dd, J = 9.2, 2.6 Hz, 1 H), 8.55 (d, J = 9.2 Hz, 1H), 8. 13 (d, J = 2.6 Hz, 1H), 7.89 (dd, J = 8.8, 2.6 Hz, 1 H), 7.55 (d, J = 8.8 Hz, 1H), 7.51 (s, 3H), 3.67 (d, J = 8.3 Hz, 1H), 3.45 (d, J = 8.3 Hz, 1H); HRMS- ESI (m/z) [M + H]+ calcd for C24H 14G5N4O4, 596.9452 ; found, 596.9441 ; IR (thin film) 3341, 3074, 1673, 1568, 1545, 1509, 1473, 1413 cm 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Cyano-2-bromo-5-nitrobenzene, its application will become more common.

Reference:
Patent; DOW AGROSCIENCES LLC; HEEMSTRA, Ronald J.; ROSS, Ronald; DEKORVER, Kyle A.; GRAY, Kaitlyn; KNUEPPEL, Daniel I.; VEDNOR, Peter; MARTIN, Timothy P.; ECKELBARGER, Joseph D.; DAEUBLE, John F.; HUNTER, Ricky; DEMETER, David A.; TRULLINGER, Tony K.; BAUM, Erich W.; BENKO, Zoltan L.; CHOY, Nakyen; CROUSE, Gary D.; LI, Fangzheng; NISSEN, Jeffrey; OLSON, Monica B.; RIENER, Michelle; SPARKS, Thomas C.; WESSELS, Frank J.; YAP, Maurice C.; (981 pag.)WO2016/168059; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 134604-07-2, A common heterocyclic compound, 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, molecular formula is C7H3BrN2O2, 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.

Description for D422-(2-methylpropyl)-5-nitrobenzonitrile (D42)To a solution of isobutylboronic acid (5.89 g), 2-bromo-5-nitrobenzo nitrile (12.5 g) and Cs2C03 (35.9 g) in toluene (150 mL) and water (5 mL) stirred under nitrogen at room temperature was added solid PdCI2(dppf CH2CI2 adduct (2.248 g) in one charge. The reaction mixture was stirred at 100 C for 16 h. After cooling the reacion, the solvent was removed in vacuo. The residue was purified by column chromatography to give 2-(2-methylpropyl)-5-nitrobenzonitrile (D42) (11 g) as a light yellow oil. deltaEta (CDCI3, 400MHz): 1.00 (6H, d), 2.06 (1 H, m), 2.86 (2H, d), 7.52 (1 H, d), 8.37 (1H, dd), 8.51 (1H, d).

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; GLAXO GROUP LIMITED; LIN, Xichen; REN, Feng; ZHANG, Haibo; WO2011/113309; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts