Author: Jessica.F

Reference of 3288-99-1, These common heterocyclic compound, 3288-99-1, name is 2-(4-(tert-Butyl)phenyl)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.

In a 10 L-reaction flask equipped with a rectification column and a separating tank, 314 g (1.81 mol) of 4-tert-butylphenylacetonitrile, 300 g (1.65 mol) of 1,3,4-trimethylpyrazol-5-carboxylic acid ethyl ester, 3000 g of heptane, 225 g of diethylene glycol dimethyl ether, and 99 g of diethylene glycol monoethyl ether were added, the atmosphere was substituted with nitrogen, then azeotropic dehydration was carried out by heating at 90 to 95 C. for 1 hour. The temperature was maintained, 381 g (1.98 mol) of 28% sodium methoxide methanol solution was added dropwise over 10 hours, and the resulting mixture was further reacted for 7 hours. After cooling to 30 C. or less, 3000 g of water was added to separate out heptane phase, and the resulting aqueous phase was further washed with 600 g of heptane to separate out heptane phase. A quantitative analysis of the obtained aqueous phase with liquid chromatography showed that the aqueous phase contained 466 g (yield 91.5%) of 2-(4-tert-butylphenyl)-3-(1,3,4-trimethyl-5-pyrazolyl)-3-oxopropionitrile. After adding 2760 g of xylene to the aqueous phase, 206 g (1.98 mol) of 35% hydrochloric acid was added dropwise to be neutralized. After separating out the aqueous phase, the resulting organic phase was washed two times with 600 g of water and the aqueous phase was separated out to obtain xylene solution of 3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)propionitrile. A quantitative analysis with liquid chromatography showed that the xylene solution contained 456 g (yield 89.6%) of 3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)propionitrile.

The synthetic route of 3288-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fukuda, Kenzo; Kondo, Yasuo; Tanaka, Norio; Suzuki, Hideaki; Ohnari, Masatoshi; Nishio, Koichi; US2006/178523; (2006); A1;,
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Reference of 2941-29-9, These common heterocyclic compound, 2941-29-9, name is Cyclopentanone-2-carbonitrile, 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.

A mixture of 2-cyanocyclopentanone (20.0 g, 183 mmol, prepared as described in Fleming et al, J. Org. Chem. 2007, 72, 1431-1436 in the Supporting Information), water (24.7 ml), and sodium cyanide (14.8 g, 302 mmol) was cooled with an ice bath to a temperature of 5 °C to 10 °C. A mixture of sulfuric acid (29.3 ml, 550 mmol) and water (24.7 ml), said mixture having a temperature of 10 °C, was added drop wise within 0.5 h while stirring. The ice bath was then removed, and the mixture was stirred for 2.5 h at room temperature. Water (50 ml) was added, and the mixture was extracted with ethyl acetate (3 x 100 ml). The combined extracts were dried with magnesium sulfate, and pyridine (51 ml, 631 mmol) was added. The solution was cooled with an ice bath to a temperature of 5 °C to 10 °C, and acetyl chloride (40.0 ml, 561 mmol) was added drop wise. The resulting mixture was stirred at 0 °C for 2 h, and then at room temperature overnight. After filtration and concentration under reduced pressure, toluene (100 ml) and ethyldiisopropylamine (94 ml, 553 mmol) were added to the residue, and the mixture was stirred at 100 °C for 6 h, and at room temperature overnight. The mixture was poured into a mixture of aqueous, concentrated hydrochloric acid (68 ml) and water (70 ml), phases were separated, the aqueous phase was extracted with ethyl acetate (3 x 150 ml), the combined extracts were washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure to yield 22.5 g of a dark oil. Distillation (2 mbar) yielded 8.6 g (40percent) of compound of formula (II) (bp 66-71 °C). 1H NMR (CDCls, 400 MHz) compound of formula (II): delta 2.17 (quint, J = 7 Hz, 2H), 2.83 (t, J = 7 Hz, 4H).

The synthetic route of 2941-29-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LONZA LTD; ZARAGOZA DOERWALD, Florencio; WO2013/102634; (2013); A1;,
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Application of 330793-38-9, 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. 330793-38-9, name is 4-Bromo-2-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step A: 2-(Methyoxy)-4-prop-2-en-l-ylbenzonitrile To a 50 mL flask containing a stir bar were added 2-methoxy-4-bromobenzonitrile (0.30 g, 1.4 mmol), palladium tetrakis (82 mg, 0.071 mmol), allyltri-n-butyltin (0.88 mL, 2.8 mmol), and lithium chloride (0.12 g, 2.8 mmol). The resulting mixture was then dissolved in anhydrous toluene (16 mL); the flask was placed in an oil bath and heated at 130 °C. LC as well as TLC (hexanes/EtOAc =1/0.3) indicated that reaction had gone to completion. The flask was taken out of the oil bath and cooled to room temperature. To the flask was added EtOAc (40 mL) and the mixture was transferred into a separatory funnel and washed with brine. The organic phase was dried over Na2S04, filtered and concentrated to dryness. It was then dissolved in DCM and absorbed into silica gel. The slica gel was then loaded onto a silica column for separation with the solvent systems of hexanes/EtOAc (1/0.3) to provide 2-(methyloxy)-4-prop-2-en-l- ylbenzonitrile. LC-MS (IE, m/z): 174 [M + 1]+.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; WO2013/39802; (2013); A1;,
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Application of 98730-77-9, 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. 98730-77-9, name is 1-(Hydroxymethyl)cyclopropanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A stirred mixture of 1-(hydroxymethyl)cyclopropanecarbonitrile (24.30 mmol, 2.36 g) in dichloromethane (30 mL) was treated with triethylamine (48.6 mmol, 6.83 mL, 4.92 g) and portionwise with methanesulfonyl chloride (31.6 mmol, 2.445 mL, 3.62 g) keeping the reaction mixture at 0 C. The solution was allowed to stir for 1 hour then diluted with saturated sodium hydrogencarbonate and extracted with 10% methanol/dichloromethane (*3). The organic layers were combined and concentrated under reduced pressure to give the intermediate (1-cyanocyclopropyl)methyl methanesulfonate (3.77 g). 1H NMR (CDCL3, 400 MHz): delta 1.18 (2H, m), 1.46 (2H, m), 3.14 (3H, s), 4.18 (2H, s)

The chemical industry reduces the impact on the environment during synthesis 1-(Hydroxymethyl)cyclopropanecarbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; N.V. Organon and pharmacopeia, Inc.; US2009/264416; (2009); A1;,
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Electric Literature of 50397-74-5, 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. 50397-74-5 name is 4-Amino-3-bromobenzonitrile, 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.

An ethanolic solution (5 mL) of 4-amino-3-bromobenzonitrile (L3, 1 mmol, 0.197 g) was added to ethanolicsolution (5 mL) of AgNO3 (0.6 mmol, 0.1 g). The test tube was covered with a perforated foil. Afterkeeping the solution in air for 4 days, light yellow crystals of 3 suitable for structure determinationwere obtained. Yield 80%, m.p. 130-132 C. Anal. Calcd for C21H15AgBr3N7O3: C, 33.15; H, 1.99; N, 12.88%. Found: C, 33.14; H, 1.97; N, 12.89%. IR (KBr, cm-1): 3481 (m), 3360 (s), 3215 (w), 2628 (w), 2221 (s), 1769(w), 1633 (s), 1594 (m), 1507 (s), 1388 (s). 1H NMR (400 MHz, DMSO) delta/ppm: 7.83 (d, J = 1.9 Hz, 1H), 7.45(dd, J = 8.5, 1.9 Hz, 1H), 6.82 (d, J = 8.5 Hz, 1H), 6.37 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-bromobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Qian, Wei; Yuan, Hao-Kun; Zhang, Ran; Fang, Rui-Qin; Journal of Coordination Chemistry; vol. 69; 23; (2016); p. 3593 – 3602;,
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Related Products of 1835-65-0, 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 1835-65-0 as follows.

Nickel complexes 3?6. A mixture of 1.00 g (3.2 mmol) of nitrile 1, 0.64 g (3.2 mmol) of nitrile 2, and 0.50 g (2.0 mmol) of nickel(II) acetate tetrahydrate was stirred during 1 h at 210 °C. After cooling the reaction mixture, it was dissolved in 50 mL of dichloromethane and filtered through a 5 cm layer of type II alumina. The solvent was distilled off, and the residue was purified by column chromatography on Kieselgel 60 silica gel (Merck). First, complexes 3 and 4 were isolated using dichloromethane as eluent, and then complexes 5 and 6 were isolated using a 95 : 5 (v/v) mixture of dichloromethane and ethanol as eluent.

According to the analysis of related databases, 1835-65-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Koptyaev; Galanin; Shaposhnikov; Russian Journal of General Chemistry; vol. 86; 4; (2016); p. 854 – 858; Zh. Obshch. Khim.; vol. 86; 4; (2016); p. 667 – 671,5;,
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Related Products of 13388-75-5, 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. 13388-75-5, name is 2-(3,5-Dimethoxyphenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A 50 mL round-bottomed flask was charged with 3 (0.177 g, 1 mmol), aromatic aldehyde or substituted aromatic aldehyde (1 mmol) and 10 mL methanol with stirring, and the mixture was heated to 60 C. After 30 min, sodium methoxide (0.027 g, 0.5 mmol) was added to the mixture and keep the temperature for 4-6 h. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to RT, and the precipitate was separated by filter and recrystallized from methanol to give 4a-4z and 5a-5d.

The chemical industry reduces the impact on the environment during synthesis 2-(3,5-Dimethoxyphenyl)acetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ma, Jun; Li, Jiajun; Tian, Yu-Shun; Bioorganic and Medicinal Chemistry Letters; vol. 27; 1; (2017); p. 81 – 85;,
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These common heterocyclic compound, 50594-78-0, name is 5-Fluoro-2-nitrobenzonitrile, 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. Safety of 5-Fluoro-2-nitrobenzonitrile

The 4-chloro-6-(1,2,4-triazol-1-yl)quinazoline used as a starting material was obtained as follows: A mixture of 5-fluoro-2-nitrobenzonitrile (3 g), 1,2,4-triazole (4.92 g), triethylamine (9.9 ml) and DMSO (50 ml) was stirred and heated to 85 C. for 16 hours. The mixture was cooled to ambient temperature and water was added. The precipitate was isolated and dried to give 2-nitro-5-(1,2,4-triazol-1-yl)benzonitrile (1.9 g) which was used without further purification.

The synthetic route of 5-Fluoro-2-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zeneca Limited; US5955464; (1999); A;,
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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;,
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Synthetic Route of 873-32-5, A common heterocyclic compound, 873-32-5, name is 2-Chlorobenzonitrile, molecular formula is C7H4ClN, 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.

General procedure: An oven-dried reaction tube was charged with Ni(MOTPP)2(1-naphthyl)Cl (2mol%, relative to aryl chloride), K3PO4 (3 equiv., relative to aryl chloride), and phenylboronic acid (1.5 equiv., relative to aryl chloride). Solid aryl chlorides (0.5mmol) were also added at this time. The tube was evacuated and purged with nitrogen for three times. 1,4-dioxane (2mL) and degassed water (0.2mL) were added via syringe. Liquid aryl chlorides were also added via syringe with the solvents. The mixture was stirred at 100C for 1h under a nitrogen atmosphere, and then cooled to room temperature. The reaction mixture was extracted with ethyl acetate, and the organic layers were dried over anhydrous Na2SO4. The organic phase was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel with hexane/ethylacetate as the eluent to afford the desired product. The products were identified by gas chromatography and NMR spectra.

The synthetic route of 873-32-5 has been constantly updated, and we look forward to future research findings.

Reference:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts