Category: 154607-01-9

Application of 154607-01-9,Some common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, molecular formula is C7H3BrClN, 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.

1-(Benzo[d][1,3]dioxol-5-yl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxamide (0.084 g, 0.20 mmol), 4-bromo-2-chlorobenzonitrile (0.043 g, 0.20 mmol), aqueous potassium carbonate (520 muL, 1M), FibreCat 1007 (7 mg), and DMF (1 mL) were combined. The mixture was heated at 80 C. for 18 hours. After cooling, the mixture was filtered and purified by preparative HPLC to provide 1-(benzo[d][1,3]dioxol-5-yl)-N-(3′-chloro-4′-cyano-6-methylbiphenyl-3-yl)cyclopropanecarboxamide.

The synthetic route of 154607-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H3BrClN

Reference Example 14; 2-chloro-4-(1H-pyrazol-4-yl)benzonitrile tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (1.53 g), 4-bromo-2-chlorobenzonitrile (1.43 g) and triethylamine (1.45 mL) were dissolved in THF-water (6:1, 11.7 mL), and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloride dichloromethane complex (1:1) (127.4 mg) was added under a nitrogen atmosphere. The reaction mixture was stirred with heating under reflux for 3 hr, and the mixture was cooled to room temperature and TFA (20 mL) was added. The reaction mixture was stirred at room temperature for 1.5 hr, and concentrated. 1 mol/L Aqueous sodium hydroxide solution was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by column chromatography (hexane-ethyl acetate) to give the title compound (808.6 mg) as pale-orange crystals.1H-NMR (CDCl3) delta: 7.80 (1H, dd), 7.93 (1H, d), 8.05 (1H, d), 8.22 (1H, brs), 8.44 (1H, brs), 13.27 (1H, brs).

According to the analysis of related databases, 154607-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/270359; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, 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. COA of Formula: C7H3BrClN

Preparation of Intermediate 4-Bromo-2-chloro-benzaldehvde (l-3a):The 4-Bromo-2-chloro-benzaldehyde was prepared using procedures described in J. Med. Chem. 1981, 24, 1155-1161.4-bromo-2-chloro-benzonitrile (7.05g, 32.5 mmol) was dissolved in toluene (60 mL) and dichloromethane (1OmL) and cooled to -600C as a 1.5M solution of diisobutylaluminum hydride in toluene (33.4 ml, 49.8 mmol) was added dropwise over 30 minutes keeping the temperature between -60 and – 500C. The reaction was allowed to warm slowly to room temperature and stirred for an additional 3 hours. The reaction was quenched using ethyl acetate and stirred for 20 minutes before the addition of 1 N hydrochloric acid at O0C. The reaction was then allowed to warm slowly to room temperature. The reaction was extracted using ethyl acetate (2 times). Removal of the solvent provided the title compound (l-3a). 1H NMR (CDCI3): delta 7.52 (dd, 1H), 7.64 (d, 1H), 7.77 (d, 1H), 10.4 (s, 1 H)

The synthetic route of 4-Bromo-2-chlorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/59335; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 154607-01-9, 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. 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Bromo-2-chloro-cyanobenzne (2.Og, 9.3 mmol) and sodium perborate (4.3g, 28 mmol) were dissolved in dioxane (40ml), water (40ml) and heated at reflux for 1 hour. An extra 2.0 g of perborate was added and the reaction was refluxed for 1 hour. The reaction was cooled, extracted with DCM (2 x 100 ml), dried and the solvent was removed in vacuo to yield a white solid. Ether was added to dissolve any remaining starting material and the solid was stirred for 10 minutes and filtered (1.35g, 62%). NMR (299.954 MHz, CDCl3) 12.61 (s, IH), 12.50 (s, IH), 12.38 – 12.31 (m, 2H), 12.13 (d, IH).

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-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/64251; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, molecular formula is C7H3BrClN, 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. SDS of cas: 154607-01-9

3-Chloro-2′,4′-difluorobiphenyl-4-carbonitrile (EM-4283): In a round bottom flask, 4-bromo-2-chlorobenzonitrile (3 g, 13.85 mmol), 2,4-difluorophenylboronic acid (2.63 g, 16.63 mmol) and K3PO4 (8.83 g, 41.56 mmol) were added in dry DMF (50 mL). The mixture was purged under argon for 30 min and Pd(PPh3)4 (1.6 g, 1.38 mmol) was added. The mixture was heated for 48 hr at 80 C. Water (100 mL) was added and the aq layer was extracted with CH2Cl2(3*50 mL). The organic layer was washed with brine (3*50 mL), dried, evaporated and purified on silica gel (EtOAc/hexanes:1/19) to give the product (1 g, 29%), 1H.NMR (acetone-d6) delta: 7.2-7.28 (m, 2H), 7.72-7.79 (m, 2H), 7.91 (t, 1H, J=1.4 Hz), 8.02 (d, 1H, J=8.1 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 154607-01-9, its application will become more common.

Reference:
Patent; Endorecherche, Inc.; US2004/6134; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 154607-01-9, A common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, molecular formula is C7H3BrClN, 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 50 mL round bottom flask was added BH3-THF (1.0 M in THF, 32.5 mL, 32.5 mmol) and 4-bromo-2-chlorobenzonitrile (1.76 g, 8.13 mmol) in THF (10 mL). The mixture was heated to reflux for 2 hours. The reaction mixture was quenched by the addition of an aqueous HCl solution (10 wt % yield). The pH was adjusted to 8 by adding an aqueous solution of NaOH (5 wt % yield) and extracted with dichloromethane. The organic layer was dried, filtered and concentrated to afford (4-bromo-2-chloro-phenyl)methanamine (1.62 g, 90% yield), which was used in the next step without further purification. LCMS (ESI) [M+H]+=220.0

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; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 154607-01-9,Some common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, molecular formula is C7H3BrClN, 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.

1-(Benzo[d][1,3]dioxol-5-yl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxamide (0.084 g, 0.20 mmol), 4-bromo-2-chlorobenzonitrile (0.043 g, 0.20 mmol), aqueous potassium carbonate (520 muL, 1M), FibreCat 1007 (7 mg), and DMF (1 mL) were combined. The mixture was heated at 80 C. for 18 hours. After cooling, the mixture was filtered and purified by preparative HPLC to provide 1-(benzo[d][1,3]dioxol-5-yl)-N-(3′-chloro-4′-cyano-6-methylbiphenyl-3-yl)cyclopropanecarboxamide.

The synthetic route of 154607-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, 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 154607-01-9, name: 4-Bromo-2-chlorobenzonitrile

A mixture of .4-bromo-2-chlorobenzonitrile (1.082 g, 5 mmol), 5-(4,4,5,5-tetramethyl- 1.3,2«dtoxaborolan-2-yl)mcotinaldehyde (1.165 g, 5.00 mmol), Pd(PPh3J4 (0.144 g. 0.125 mmol), sodium carbonate (2.5 ml, 5.00 mmo.) in 1,4-dioxane (20 mL) was heated to reflux for 6 h. After cooling to room temperature, the solid was filtered and washed by ethyl acetate and water. After drying under vacurnn, yellow powder was collected (1 g). 1H NMR (400 MHz. CDCI3): S 7.63 (dd, J = 1.68, 8 Hz, 1H)1 7.79 (d, J * 1.68 Hz, 1H), 7.83 (d, J » 8 Hz, 1H)1 8.35 (dd, J = 2.24 Hz, 2.04 Hz. 1H)1 9.07 (d, J * 2.36 Hz, 1H), 9.15 (d, J = 1.88 Hz. 1H)1 10.22 (s, 1H).

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