Category: 191014-55-8

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. 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H6FNO

4-Fluoro-2-hydroxyben?onitrile. A mixture of intermediate 127, 4-fluoro-2- methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130 C for 18 hrs. After cooling, ice water (~50 mL)was added and the resulting mixture extracted with ether (20 mL x 2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) delta ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (IH, dd, J = 7 Hz, J = 8.5 Hz, Ar-H), 11.64 (IH, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) delta ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35.HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199.

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
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Nitriles – Chemistry LibreTexts

Application of 191014-55-8, The chemical industry reduces the impact on the environment during synthesis 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of (4S,5S)-4-hydroxy-5-methylpyrrolidin-2-one 7 33 (7.00 g, 60.8 mmol) in THF (120 mL) was added sodium bis(2-methoxyethoxy)aluminium dihydride (70% in toluene, 59.7 mL, 215 mmol) slowly at 5 C. After stirring at 70 C for 3 h, the reaction mixture was cooled to 5 C followed by addition of sodium carbonate decahydrate (26.1 g, 91.2 mmol). The mixture was stirred at room temperature for 16 h, diluted with THF, and the precipitate was filtered off. The filtrate was concentrated in vacuo, and the residue was dissolved in DMSO (80 mL). To the solution was added lithium carbonate (8.99 g, 122 mmol) and 2-chloro-4-fluorobenzonitrile (9.46 g, 60.9 mmol), and the mixture was stirred at 100 C for 1 h. The mixture was diluted with EtOAc and H2O, and the organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc) to give 10 (10.7 g, 74%) as a colorless solid. 1H NMR (300 MHz, CDCl3) delta: 1.18 (3H, d, J = 6.6 Hz), 1.82 (1H, d, J = 5.5 Hz), 2.01-2.14 (1H, m), 2.25-2.35 (1H, m), 3.19-3.28 (1H, m), 3.43-3.51 (1H, m), 3.89-3.98 (1H, m), 4.43-4.52 (1H, m), 6.43 (1H, dd, J = 8.9 and 2.4 Hz), 6.56 (1H, d, J = 2.4 Hz), 7.42 (1H, d, J = 8.9 Hz). MS (ESI) m/z 237 [(M+H)+].

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-Fluoro-2-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yamamoto, Satoshi; Kobayashi, Hiromi; Kaku, Tomohiro; Aikawa, Katsuji; Hara, Takahito; Yamaoka, Masuo; Kanzaki, Naoyuki; Hasuoka, Atsushi; Baba, Atsuo; Ito, Mitsuhiro; Bioorganic and Medicinal Chemistry; vol. 21; 1; (2013); p. 70 – 83;,
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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. 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 191014-55-8

4-Fluoro-2-hydroxyben?onitrile. A mixture of intermediate 127, 4-fluoro-2- methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130 C for 18 hrs. After cooling, ice water (~50 mL)was added and the resulting mixture extracted with ether (20 mL x 2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) delta ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (IH, dd, J = 7 Hz, J = 8.5 Hz, Ar-H), 11.64 (IH, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) delta ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35.HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199.

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, 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. Computed Properties of C8H6FNO

Pyrazolospiroketone Preparation 11; 2-Methoxy-4-(3′-methyl-7′-oxo-6′.7′-dihvdro-2’H-spirorpiperidine-4,5′-pyranor3.2-clPyrazol1-2′-; To a solution of 4-fluoro-2-methoxybenzonitrile (100 g, 0.662 mol) in ethanol (0.66 L) was added hydrazine monohydrate (331 g, 0.321 L, 6.62 mol). The mixture was heated at reflux overnight. The reaction was cooled to room temperature, diluted with water (750 mL), stirred for 1.5 hours and the resulting solids were collected by filtration. The solids were rinsed with water (2 x 250 mL) and air dried for 3 hours. The solids were then dried in a vacuum oven at 45 QC. The material was dissolved in dioxane (2 L) and HCI gas was bubbled through for 30 minutes. The resulting solids were filtered and washed with methyl tert-butyl ether (2 x 1 L). The solids were air dried for 1 hour and the resulting solids were dried in a vacuum oven at 45 QC to provide -hydrazino-2-methoxybenzonitrile hydrochloride (115.6 g, 87.5%).

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER, INC.; WO2009/144554; (2009); A1;,
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Electric Literature of 191014-55-8, A common heterocyclic compound, 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, molecular formula is C8H6FNO, 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 1 g of 4-fluoro-2-methoxy-benzonitrile in 15 mL of dichloroethane was added 1.1 g of aluminum trichloride. The resulting mixture was refluxed for 1 day then poured slowly into water and extracted with ethyl acetate. The organic extracts were washed twice with 10% aqueous solution of sodium hydroxide. The combined basic layers were washed twice with ethyl acetate, acidified with concentrated aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic extracts were washed with water, with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 0.78 g of 4-fluoro-2-hydroxy-benzonitrile as a white solid.C7H4FNO (137.11), MS (ESI): 138.17 (M+H+).

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2008/261979; (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 191014-55-8 as follows. Recommanded Product: 4-Fluoro-2-methoxybenzonitrile

To a solution of 0.7 g of 1-[4-methyl-2-(4-trifluoromethyl-cyclohexyl)-oxazol-5-yl]-propan-1-ol in 3 mL of dimethylformamide at 5 C. was added 113 mg of a 55% suspension of sodium hydride in mineral oil. The reaction mixture was stirred for 30 minutes at 5 C. The resulting mixture was slowly added to a solution of 429 mg of 4-fluoro-2-methoxy-benzonitrile in 1 mL of dimethylformamide at 5 C. The resulting mixture was stirred at 5 C. allowing the temperature to warm up to room temperature. It was then heated in a sealed tube to 60 C. under microwave irradiation for 15 minutes. After allowing it to cool down to room temperature, the mixture was poured into water and extracted with dichloromethane. The organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient from heptane 100 to heptane 50/ethyl acetate 50) to give 1.05 g of 2-methoxy-4-{1-[4-methyl-2-(trans-1,4-trifluoromethyl-cyclohexyl)-oxazol-5-yl]-propoxy}-benzonitrile.C22H25F3N2O3 (422.45), MS (ESI): (M+H+) 423.4 (M+H+).

According to the analysis of related databases, 191014-55-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2008/261979; (2008); 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. 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Formula: C8H6FNO

A solution of lithium diisopropylamide (18.20 mL, 36.39 mmol) in THF (25 mL) was stirred at -78 C for =10 minutes. A solution of 4-fluoro-2-methoxybenzonitrile (5.00 g, 33.08 mmol) in THF (15 mL) was added dropwise over 10 minutes and the resulting mixturewas stirred at -78 for 1 h. The reaction mixture was poured over dry ice (excess) and then allowed to warm to room temperature over several hours. After all the dry ice had evaporated the crude product was dissolved in DCM (125 mL) and extracted with saturated aqueous NaHCO3 (2 x 70 mL). The combined aqueous extracts were acidified with conc. HC1 to pH = =2, extracted with DCM (2 x 75 mL). The combined organic layers were dried(Na2SO4) and concentrated at reduced pressure to provide the product as a light yellow solid (4.5 g, 69%). ?H NMR (400MHz, DMSO-d6) oe = 7.97 (dd, J = 6.3, 8.6 Hz, 1H), 7.26 (t, J = 8.8 Hz, 1H), 4.00 (s, 3H).

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DART NEUROSCIENCE, LLC; BASINGER, Jillian; BOOKSER, Brett; CHEN, Mi; CHUNG, DeMichael; GUPTA, Varsha; HUDSON, Andrew; KAPLAN, Alan; NA, James; RENICK, Joel; SANTORA, Vincent; WO2015/164520; (2015); 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. 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, A new synthetic method of this compound is introduced below., name: 4-Fluoro-2-methoxybenzonitrile

To a mixture of 4-fluoro-2-methoxybenzonitrile, (800 mg, 5.3 mmol) and conc.HCl (0.53 mL, 6.36 mmol, 1.2 eq.) in ethanol (20 mL) was added 10% Pd-C (100 mg; Aldrich), and the mixture hydrogenated at 1 atm hydrogen for 15 hrs at room temperature. To this mixture was added an additional amount of conc.HCl (1 mL) and 10% Pd-C (200 mg) and the reaction allowed to continue for another 40 hrs. The mixture was filtered through Celite and the filtrate concentrated in vacuo to dryness. The residue was triturated with ether to provide the title compound (895 mg, Yield 88%) as a white powder: 1H NMR (CDCl3, 500 MHz) delta ppm: 3.84 (3H, s, OMe), 3.91 (2H, d, J=5.5 Hz, N-CH2), 6.81 (1H, dt, J=2.5 Hz, J=J=8.5 Hz, Ar-H), 6.99 (1H, dd, J=2.5 Hz, J=11.3 Hz, Ar-H), 7.47 (1H, dd, J=7 Hz, J=8.5 Hz, Ar-H); 13C NMR (CDCl3, 125.8 Hz) delta ppm: 36.76, 56.03, 99.30, 99.51 106.28, 106.45, 117.93, 117.95, 131.60, 131.69, 158.56, 158.64, 162.28, 164.22. HRMS (ESI) calcd for C8H11FNO (M+H) 156.0825, found 156.0830.

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; Bristol-Myers Squibb Company; US2007/111984; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, 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 191014-55-8, category: nitriles-buliding-blocks

To a mixture of intermediate 127, 4-fluoro-2-methoxybenzonitrile, (800 mg, 5.3 mmol) and conc.HCl (0.53 mL, 6.36 mmol, 1.2 eq.) in ethanol (20 mL) was added 10% Pd-C (100 mg; Aldrich), and the mixture hydrogenated at 1 atm hydrogen for 15 hrs at room temperature. To this mixture was added an additional amount of conc.HCl (1 mL) and 10% Pd-C (200 mg) and the reaction allowed to continue for another 40 hrs. The mixture was filtered through Celite and the filtrate concentrated in vacuo to dryness. The residue was triturated with ether to provide the title compound (895 mg, Yield 88%) as a white powder: 1H NMR (CDCl3, 500 MHz) ? ppm: 3.84 (3H, s, OMe), 3.91 (2H, d, J=5.5 Hz, N-CH2), 6.81 (1H, dt, J=2.5 Hz, J=J=8.5 Hz, Ar-H), 6.99 (1H, dd, J=2.5 Hz, J=11.3 Hz, Ar-H), 7.47 (1H, dd, J=7 Hz, J=8.5 Hz, Ar-H); 3C NMR (CDCl3, 125.8 Hz) ? ppm: 36.76, 56.03, 99.30, 99.51 106.28, 106.45, 117.93, 117.95, 131.60, 131.69, 158.56, 158.64, 162.28, 164.22. HRMS (ESI) calcd for C8H11FNO (M+H) 156.0825, found 156.0830.

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; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 191014-55-8,Some common heterocyclic compound, 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, molecular formula is C8H6FNO, 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.

(S)-4-bromo-2,3-dihydro-1H-inden-1-amine (1.0 g, 4.7 mmol), 4-fluoro-2-methoxybenzonitrile (0.89 g, 5.89 mmol), and N,N-Diisopropylethylamine (0.90 g, 7.1 mmol), were suspended in N-Methyl-2-pyrrolidone (5 mL). The suspension was stirred and heated to 115 C. for 48 h. The reaction was cooled to room temperature, and diluted with ethyl acetate and diethyl ether. The mixture was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated. The product was purified by column chromatography (ethyl acetate/hexanes) to provide (S)-4-((4-bromo-2,3-dihydro-1H-inden-1-yl)amino)-2-methoxybenzonitrile. (S)-4-((4-bromo-2,3-dihydro-1H-inden-1-yl)amino)-5-chloro-2-methoxybenzonitrile:

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Sciences, Inc.; Aktoudianakis, Evangelos; Cho, Aesop; Graupe, Michael; Lad, Lateshkumar Thakorlal; Machicao Tello, Paulo A.; Medley, Jonathan William; Metobo, Samuel E.; Naduthambi, Devan; Phillips, Barton W.; Simonovich, Scott Preston; Wang, Peiyuan; Watkins, William J.; Xu, Jie; Yang, Kin Shing; Ziebenhaus, Christopher Allen; US2020/17471; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts