Category: 179898-34-1

Synthetic Route of 179898-34-1, These common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-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.

Step 1 A solution of 3-bromo-5-fluorobenzonitrile (CIV) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20 C. Then it was stirred at 80 C. for 2 h, HCl (6 N, 100 mL) was added to the mixture slowly at 20 C. The mixture was stirred at 80 C. for 1 h, then it was washed with EtOAc (300 ml). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL*3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (CV) (24.0 g, 117.62 mmol, 53.5% yield). 1H NMR (CDCl3, 300 MHz) 3.86 (s, 2H), 7.01 (d, J=8 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN m/z 203.9 (Br79M+H).

Statistics shows that 3-Bromo-5-fluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 179898-34-1.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (2016); A1;,
Nitrile – Wikipedia,
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Related Products of 179898-34-1, A common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, molecular formula is C7H3BrFN, 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 57 3′-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-fluoro-3-biphenylcarbonitrile 3-Bromo-5-fluorobenzonitrile (5.00 g, 25.0 mmol), Pd(OAc)2 (0.15 g), PPh3 (0.60 g) and K2CO3 (5.18 g, 37.5 mmol) were dissolved in dioxane (60 mL). The mixture was heated at 70 C. for 30 min, then [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (7.99 g, 30.0 mmol) was added. The mixture reaction was stirred at reflux overnight. The solvent was removed under reduced pressure, then diluted with CH2Cl2 (100 mL). The organic layer was washed with water (50 mL) and brine (50 mL). And the organic layer was dried over Na2SO4. The product 3′-({[(1,1-dimethylethyl) (dimethyl)silyl]oxy}methyl)-5-fluoro-3-biphenylcarbonitrile (5.10 g, 60%) was purified by flash column chromatography. 1H NMR (400 MHz, CDCl3): delta 7.67 (t, J=5.2 Hz, 1H), 7.54-7.32 (m, 5H), 4.81 (s, 2H), 0.94 (s, 9H), 0.13 (s, 6H).

The synthetic route of 179898-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Group Limited; US2009/197871; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 179898-34-1, 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 179898-34-1 as follows.

Example 54 3 ‘-({ [(1 ,1-Dimethylethyl)(dimethyl)silyl] oxy} methyl)-5-fluoro- 3- biphenylcarbonitrile3-bromo-5-fluorobenzonitrile (5.00 g, 25.0 mmol), Pd(OAc)2 (0.15 g), PPh3 (0.60 g) and K2CO3 (5.18 g, 37.5 mmol) were dissolved in dioxane (60 mL). The mixture was heated at 700C for 30 min, then [3 -({[(l,l-dimethylethyl)(dimethyl)silyl] oxy} methyl) phenyljboronic acid (7.99 g, 30.0 mmol) was added. The mixture reaction was stirred at reflux overnight. The solvent was removed under reduced pressure, then diluted with CH2Cl2 (100 mL). The organic layer was washed with water (50 mL) and brine (50 mL). And the organic layer was dried over Na2SOzI. The product 3’-({[(l,l-dimethylethyl) (dimethyl)silyl]oxy} methyl)-5-fluoro-3-biphenylcarbonitrile (5.10 g, 60%) was purified by flash column chomatography. 1H NMR (400 MHz, CDCl3) delta 7.67 (t, J=5.2 Hz, 1 H), 7.54-7.32 (m, 5 H), 4.81 (s, 2 H), 0.94 (s, 9 H), 0.13 (s, 6 H).

According to the analysis of related databases, 179898-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/100169; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A common compound: 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 179898-34-1

(i) 3-bromo-5-methoxybenzonitrile Sodium methoxide (2.02 g) was added to a stirred solution of 3-fluoro-5-bromobenzonitile (5.0 g) in DMPU (20 ml) and stirred at RT for 2 h. The reaction was diluted with water and the resulting solid formed was filtered and washed with water, then dried in vacuo to give the subtitle compound (5.10 g). 1H NMR DMSO-d6: 7.39-7.38 (1H, s), 7.30-7.26 (1H, m), 7.11 (1H, s), 3.83 (3H, s).

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, 179898-34-1, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2008/293775; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 179898-34-1 as follows. 179898-34-1

Example 1; 3-fluoro-5-{5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridin-2-yl}benzonitrile; Step 1: 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile; 3-Bromo-5-fluorobenzonitrile (30.0 mmol, 9.23 g), bis(pinacolato)diboron (30.0 mmol, 7.62 g), PdCl2(dppf)2 (1:1 complex with dichloromethane, 1.2 mmol, 980 mg), and potassium acetate (105 mmol, 10.3 g) were combined in deoxygenated dioxane (150 mL) and heated at 80 C. for 4 hrs, at which time the reaction was determined to be complete by GC/MS analysis. The reaction was cooled to room temperature, and poured in to a separatory funnel containing EtOAc (300 mL) and water (200 mL). The aqueous layer was back extracted with EtOAc (75 mL), and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was carried on to the next step with out further purification or characterization.

According to the analysis of related databases, 179898-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cosford, Nicholas D.; Seiders, Thomas J.; Payne, Joseph; Roppe, Jeffrey R.; Huang, Dehua; Smith, Nicholas D.; Poon, Steve F.; King, Chris; Eastman, Brian W.; Wang, Bowei; Arruda, Jeannie M.; Vernier, Jean-Michel; Zhao, Xiumin; US2009/203903; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding some certain compound to certain chemical reactions, such as: 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, 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 179898-34-1. 179898-34-1

Example 15 1,1-Dimethylethyl[(3-bromo-5-fluorophenyl)methyl]carbamate NaBH4 (1.99 g, 52.5 mmol) was cautiously added to a solution of NiCl2 (1.36 g, 10.5 mmol), Boc2O (4.58 g, 21.0 mmol) and 3-bromo-5-fluorobenzonitrile (2.10 g, 10.5 mmol) in absolute ethanol (30 mL) at 0 C. (vigorous reaction with the formation of a black precipitate). Once the reaction had subsided the mixture was left to stir at room temperature for 30 min. Ethanol was removed under reduced pressure and the precipitate was dissolved in EtOAc, filtered and repeatedly washed with EtOAc. The combined organic phases were washed with saturated NaHCO3, and dried (Na2SO4). After removing the solvent, the product, was purified by flash column chomatography to yield 1,1-dimethylethyl[(3-bromo-5-fluorophenyl)methyl]carbamate (2.20 g, 69%). 1H NMR (400 MHz, CDCl3) delta 1.46 (S, 9H), 4.28-4.32 (m, 2H), 4.87 (br, 1H), 6.93-7.29 (m, 3H); 13C NMR (100 MHz, CDCl3) delta 20.3, 43.6, 44.1, 79.7, 80.0, 113.0, 114.0, 117.7, 122.5, 126.0, 123.0, 141.7, 155.9, 161.5, 164.0.

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 3-Bromo-5-fluorobenzonitrile.

Reference:
Patent; Glaxo Group Limited; US2009/203677; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

179898-34-1, 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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3-bromo-5-fluorobenzonitrile (LXVI) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20C. Then it was stirred at 80C for 2 h, HC1 (6 N, 100 mL) was added to the mixture slowly at 20C. The mixture was stirred at 80C for 1 h, then it was washed with EtOAc (300 mL). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL x 3). The combined organic layers were dried over anhydrous Na2504 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (LXVII) (24.0 g, 117.62 mmol, 53.5% yield). ?H NMR (CDC13, 300 MHz) ppm 3.86 (s, 2H), 7.01 (d, J=8Hz, 1H), 7.12 (d, J=8Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN mlz 203.9 (Br79M+H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (254 pag.)WO2017/23993; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, 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. 179898-34-1

A solution of 3-bromo-5-fluorobenzonitrile (2.5g, 12.5mmol), (trimethylsilyl)acetylene(2.86ml,20mmol), bis(acetate)bis(triphenylphoshpino)Palladium(II) (936mg, 1.25mmol) and triethylamine (35ml) in toluene (35ml) was degassed by bubbling nitrogen through the solution and then stirred at 950C for 30 minutes. Filtration and concentration to yield a crude product. It was diluted with EtOAc (150ml). The organic phase was washed with saturated NaHCO3 solution (50ml), brine (50ml) and the organic layer was dried over sodium sulfate. Filtration EPO and concentration to yield a product A293.1 (2Ag, 88%). HPLC: 95%, retention time: 4.05 minute (condition A). LC/MS (M+H)+ = 218.2.

Statistics shows that 179898-34-1 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-5-fluorobenzonitrile.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

179898-34-1, 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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

824 mg (0.900 mmol) of tris(dibenzylideneacetone)dipalladium and 1.23 g (1.98 mmol) of rac-1,1′-binaphthalene-2,2′-diylbis(diphenylphosphane) are added to 9.00 g (45.0 mmol) of 3-bromo-5-fluorobenzenecarbonitrile in toluene (300 ml) under an argon atmosphere. After the addition of 19.5 g (54.0 mmol) of (1-ethoxyvinyl)tributylstannane, the mixture is stirred under reflux overnight. The reaction mixture is subsequently concentrated and the residue is taken up in 300 ml of THF. After the addition of 100 ml of an aqueous 2N hydrogen chloride solution the mixture is stirred at room temperature for 2 h. The reaction mixture is subsequently neutralized with a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 9:1). 7.11 g (97% of theory) of the title compound are obtained.1H-NMR (400 MHz, DMSO-d6): delta=8.28 (t, 1H), 8.18-8.14 (m, 1H), 8.08-8.04 (m, 1H), 2.65 (s, 3H).GC-MS (Method 11): Rt=3.97 min; MS (EIpos): m/z=163 [M]+.

The synthetic route of 179898-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AiCuris GmbH & Co. KG; US2011/124618; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

179898-34-1, The chemical industry reduces the impact on the environment during synthesis 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

Step A: 3-fluoro-5-formylbenzonitrile: A solution of 3-bromo-5- fluorobenzonitrile (5.00 g, 25.0 mmol) in dry THF (25 mL) was cooled to 0 C and 2M iPrMgCl (15.0 mE, 30.0 mmol) in THF was added dropwise over 5 minutes. The mixture was stirred at 0 C for 15 minutes then at ambient temperature for 1 hour. The mixture was cooled to 0 C and dry DMF (5.81 mL, 75.0 mmol) was added. The mixture was stirred for 17 hours during which time the temperature reached ambient temperature after 2 hours. The mixture was added to ice water (150 mL) and Et20 (100 mL). The biphasic mixture was stirred and treated with 6M HC1 to aqueous pH=3. The organic layer was removed and the aqueous layer extracted with Et20 (2X). The combined Et20 fractions were washed with saturated NaC1 and dried over MgSO4/activated carbon. The dried solution was filtered through a Si02 plug eluting with Et20. The filtrate was concentrated to give the title compound as a yellow solid that was dried in vacuum (3.68 g, 99%). ?H NMR (CDC13) oe 10.0 (s, 1H), 8.00 (s, 111), 7.81-7.86 (m, 111), 7.62-7.67 (m, 111).

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-5-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BRANDHUBER, Barbara, J.; KERCHER, Timothy; KOLAKOWSKI, Gabrielle, R.; WINSKI, Sharon, L.; WO2014/78323; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts