Category: 501-00-8

Electric Literature of 501-00-8, 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. 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of 1-(3-fluorophenyl)cyclohexanecarbonitrile To a solution of 2-(3-fluorophenyl)acetonitrile (100 g, 0.74 mol) in Dry DMF (1000 ml) was added 1,5-dibromopentane (170 g, 0.74 mol), NaH (65 g, 2.2 eq) was added dropwise at ice bath. After addition, the resulting mixture was vigorously stirred overnight at 50 C. The suspension was quenched by ice water carefully, extracted with ethyl acetate (3*500 ml). The combined organic solution was concentrate to afford the crude which was purified on flash column to give 1-(3-fluorophenyl)cyclohexanecarbonitrile as pale solid (100 g, 67%).

The synthetic route of 2-(3-Fluorophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Acetylon Pharmaceuticals, Inc.; Quayle, Steven Norman; Jones, Simon Stewart; Anderson, Kenneth C.; Hideshima, Teru; US2015/105358; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 501-00-8, 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. 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-(3- fluorophenyl)acetonitrile (100 g, 0.74 mol) in Dry DMF (1000 ml) was added 1,5- dibromopentane (170 g, 0.74 mol), NaH (65 g, 2.2 eq) was added dropwise at ice bath. After addition, the resulting mixture was vigorously stirred overnight at 50C. The suspension was10 quenched by ice water carefully, extracted with ethyl acetate (3*500 ml). The combined organic solution was concentrate to afford the crude which was purified on flash column to give 1-(3-fluorophenyl)cyclohexanecarbonitrile as pale solid (100 g, 67%).

The synthetic route of 2-(3-Fluorophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF MODENA AND REGGIO EMILIA; COSENZA, Maria; POZZI, Samantha; (78 pag.)WO2016/87950; (2016); 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. 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Quality Control of 2-(3-Fluorophenyl)acetonitrile

(0086) In a charge of 200 ml of methanol, 25.9 g (=0.1 mol) of aldehyde of the formula (II), where R1=-COOCH3, R4=-CH3 and R5 and R6=-CH3, and 13.5 g (=0.1 mol) of 3-fluorophenylacetonitrile were introduced. Subsequently, the pH was adjusted to around 10 with ca. 1 g of a 50% aqueous potassium hydroxide solution and the reactor contents were heated to a temperature of 60 C. and then stirred for ca. 6 hours. The mixture was then cooled to 25 C. and the reaction product isolated on a Nutsche filter. The filter cake was washed with ca. 50 ml of methanol and ca. 500 ml of water (T=90 C.). The washed product was dried in a vacuum drying cabinet at a temperature of 80 C. and a pressure of 200 mbar. (0087) Yield: 24.5 g (corresponds to 65% of theory), melting point 311 C.

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; LANXESS Deutschland GmbH; BORST, Hans-Ulrich; LINKE, Frank; MICHAELIS, Stefan; (10 pag.)US2017/349752; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, 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. Safety of 2-(3-Fluorophenyl)acetonitrile

2-Chloro-N-(2-chloroethyl)ethanaminium chloride (12.5 g, 70.2 mmol) was stirred in 351 mL of THF. To this mixture was added triethylamine (10.3 mL, 73.7 mmol) and then di-tert-butyl dicarbonate (16.1 g, 73.7 mmol), which was stirred for 19 hours. The reaction was diluted with dichloromethane (250 mL), washed with water (3 x 250 mL), and partitioned between water and dichlormethane. The organic layer was dried over sodium sulfate, filtered, and concentrated to afford tert-butyl bis(2-chloroethyl)carbamate. A mixture of 3-fluorophenylacetonitrile (200 mg, 1.48 mmol) and tert-butyl bis(2- chloroethyl)carbamate (358 mg, 1.48 mmol) was dissolved in 14.8 mL of anhydrous DMSO. The reaction was purged with a stream of nitrogen and cooled to 18 0C. To this reaction was added sodium hydride (358 mg, 1.48 mmol), which was then warmed to ambient temperature and stirred for 2 hours. The reaction was warmed to 50 0C and stirred for 17 hours. The mixture was diluted with dichloromethane (40 mL), washed with water (3 x 40 mL), and partitioned between water and dichloromethane. The organic layer was dried over sodium sulfate, filtered, concentrated, and subjected to silica gel chromatography eluting with 0-20% EtOAc in hexanes. Collection of product containing fractions and removal of solvent yielded tert-butyl 4-cyano-4- (3-fluorophenyl)piperidine- 1 -carboxylate. The title compound was prepared in a manner analogous to that described inExample 1 that gave a proton NMR spectrum consistent with theory and a high resolution mass spectrum (ES+) m/z of 406.1575 calculated for M+H+ [C23H20FiN3O3: 406.1562]: 1H NMR (500 MHz, CD3OD) delta 9.56 (d, J= 7.1 Hz, IH), 8.70 (s, IH), 8.47 (d, J= 9.0 Hz, IH), 8.18 (t, J= 7.9 Hz, IH), 7.72 (t, J= 6.8 Hz, IH), 7.46-7.51 (m, IH), 7.37 (d, J= 8.6 Hz, IH), 7.30 (d, J= 10.0 Hz, IH), 7.16 (t, J= 8.4 Hz, IH), 4.67 (bs, 2H), 3.65 (m, 2H), 3.37 (m, 2H), 2.46 (d, J= 14.2 Hz, 2H), 2.29 (m, 2H).

The synthetic route of 501-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/51715; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, 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. HPLC of Formula: C8H6FN

To a solution of compound 36-2 (346 mg, 2.56 mmol) in THF (10 niL) was added Raney Ni. Then the mixture was adjusted to PH=IO with concentrated aqueous ammonia and stirred at 30 0C overnight. TLC showed the reaction was completed. The mixture was filtered through Celite and the filtrate was concentrated to give 36-3 as a yellow oil (120 mg, yield: 34 %).

The synthetic route of 2-(3-Fluorophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY; YUAN, Junying; MA, Dawei; LIU, Junli; ZHANG, Lihong; WO2011/11522; (2011); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, 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. Product Details of 501-00-8

General procedure: General procedure for the reduction of nitrile by KBH4and CuCl2:To a 10 mL round-bottomed flask was added 2-(4-chlorophenyl)acetonitrile (0.1 5 g, 1 mmol), KBH4 (0.17 g, 3mmol), CuCl2 (0.03 g, 0.25 mmol) and 80 % isopropanol (1.6mL isopropanol and 0.4 mL water). The reaction completed in8 h at 60 C as evidenced by TLC (DCM:MeOH 10:1). Thereaction mixture was cooled to 25 C and removed the solvent.Ethyl acetate (5 mL) was added to the residue, washed withwater (1 mL) and brine (1 mL). The organic layer were dried withanhydrous Na2SO4, filtered and evaporated in vacuo to affordthe crude product.

The synthetic route of 501-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jiang, Han; Hu, Jialei; Xu, Xinliang; Zhou, Yifeng; Asian Journal of Chemistry; vol. 27; 10; (2015); p. 3564 – 3566;,
Nitrile – Wikipedia,
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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. 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 501-00-8

To a mixture of 5.8 mL (50 mmol) of 3- fluorophenylacetonitrile (5), 8.3 mL (100 mmol) of 1- bromo-2-chloroethane, and 0.23 g (1.0 mmol) of benzyltriethylammonium chloride was added 28 mL of 50% aqueous sodium hydroxide solution, and the resulting mixture was stirred at 40C for 3 hours [M. FEDORYNSKI and A. JONCZYK Org. Prep. Proc. Intl. (1995) 27,355- 3591. At this point 25 mL of ethylene glycol was added, and the mixture then was stirred at 100C for another 20 hours. After cooling to room temperature, the reaction mixture was diluted with water and then washed with ethyl acetate. The aqueous phase was adjusted to pH 2 employing hydrochloric acid and then extracted with diethyl ether. The combined extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to provide 8.1 g of 1- (3- fluorophenyl) cyclopropane-l-carboxylic acid (6). NMR (300 MHz, DMSO-D6) 12.41 (br s, 1 H), 7.37-7. 29 (m, 1 H), 7.18-7. 03 (m, 3 H), 1.45 (d of d, 2 H), 1.17 (d of d, 2 H).

According to the analysis of related databases, 501-00-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2004/43911; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, 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. COA of Formula: C8H6FN

Step 1: Methyl 4-cyano-4-(3-fluorophenyl)-3-(4-fluorophenyl)butanoate [0747] Under protective gas (Ar), 0.767 g (5.0 mmol) of (3-fluorophenyl)acetonitrile and 0.1 ml of sodium methoxide solution (30% in methanol) were added to 0.820 g (4.55 mmol) of methyl 3-(4-fluorophenyl)acrylate in 15.0 ml of toluene, and the mixture was stirred in a closed vessel at 65 C. for 15 h. The solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with in each case 25 ml of water. The combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel (ethyl acetate/heptane=20:80) gave 0.950 g (57% of theory) of the diastereomeric methyl 4-cyano-4-(3-fluorophenyl)-3-(4-fluorophenyl)butanoate (erythro:threo=54:46 according to integration of the methyl singlets in the 1H-NMR in CDCl3 at 3.66 and 3.56 ppm).

The synthetic route of 501-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Mosrin, Marc; Jakobi, Harald; Angermann, Alfred; Gatzweiler, Elmar; Haeuser-Hahn, Isolde; Heinemann, Ines; Rosinger, Christopher Hugh; Lehr, Stefan; Schnatterer, Stefan; US2014/235446; (2014); 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. 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 501-00-8

CHART B, Preparation of the amine used in Chart B, Step B-2. A stirred suspension of freshly washed and dried sodium hydride (50% by wt, 9.59 g, 200 mmol) in dry dimethyl sulfoxide (75 mL) under N2 is cooled to 0 C. A mixture of 3-fluorophenylacetonitrile (8.6 mL, 74.0 mmol) and 1,3-dibromopropane (8.3 mL, 81.4 mmol) in ether (40 mL) is then added dropwise over 35 minutes, via cannula. The resulting orange-red mixture is allowed to stir at 20-25 C. overnight. The thick reaction mixture is cooled to 0 C. and treated with isopropanol (4 mL). After stirring for 15 minutes, water (64 mL) is added in 10 mL increments and the phases are separated. The aqueous layer is extracted with ether (4*100 mL). The combined organics are washed with water (3*100mL), brine (1*100 mL), dried (MgSO4), filtered and concentrated. The product is distilled at 95 C. (1.0 torr) to afford 7.41 g of 1-(3-fluorophenyl)cyclobutanecarbonitrile. 1 H NMR (CDCl3) delta7.39 (m, 1 H), 7.19 (m, 1 H), 7.13 (m, 1 H), 7.05 (m, 1 H), 2.81 (m, 2 H), 2.60 (m, 4 H), 2.50 (m, 1 H), 2.12 (m, 1 H); 13 C NMR (CDCl3) delta164.6, 161.3, 142.2, 130.6, 130.5, 123.8, 121.37, 121.32, 115.0, 114.7, 113.0, 112.7, 77.2, 40.9, 39.9, 34.6, 17.0.

The synthetic route of 501-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Upjohn Company; US5525742; (1996); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, 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: 2-(3-Fluorophenyl)acetonitrile

The reactor was charged with palladium(II) acetate (0.160 g, 0.71 1 mmol), 2,8,9-triisobutyl- 2,5,8,9-tetraaza-l-phosphabicyclo[3.3.3]undecane (0.507 mL, 1.421 mmol), and 5-bromo-2- methyl- lH-benzo[d]imidazole (1.5 g, 7.1 1 mmol). The vessel was evacuated and refilled with N2 for 3 cycles and degassed dioxane (14.21 mL) was added, followed by NaHMDS (28.4 mL, 28.4 mmol). The reaction was stirred at 25C for 20 min before 2-(3-fluorophenyl)acetonitrile (73.3 mg, 0.543 mmol) was added. The reaction was then capped and heated at 100C for 3 h. More NaHMDS (6 mL) was added and the reaction was stirred for another 1 h; More NaHMDS (4 mL) was added and the reaction was stirred for another 1 h before it was cooled to room temperature, and quenched with water. The aqueous layer was extracted with EtOAc (3x), washed with brine, dried over MgS04, filtered, and the filtrate was concentrated in vacuo. The crude material was purified by chromatography on silica gel (eluent: 0-100% A in B. A: 10% MeOH in DCM; B: DCM.). LCMS calc. = 266.10, found = 266.04 (M+H)+.

The synthetic route of 501-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; ZHANG, Ting; CHEN, Yi-Heng; GUO, Liangqin; HRUZA, Alan; JIAN, Tianying; LI, Bing; MENG, Dongfang; PARKER, Dann, L., Jr.; SHERER, Edward, C.; WOOD, Harold, B.; SAKURADA, Isao; (130 pag.)WO2016/94260; (2016); A1;,
Nitrile – Wikipedia,
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