Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 32703-82-5, name is 6-(tert-Butyl)naphthalene-2,3-dicarbonitrile, 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 32703-82-5, HPLC of Formula: C16H14N2

A mixture of 6-tert-butyl-2,3-dicyanonaphthalene A (18.8 g, 0.08 mol), anhydrous zinc acetate B (3.7 g, 0.02 mol), dry quinoline 100 mL and DBU 12 mL was stirred at 180 deg C for 20 hr. After cooling, the mixture was poured into methanol (3500 mL). The crude product was collected by vacuum filtration, washed with methanol and purified by Soxhlet extraction with methanol for 2 days. Finally, the dark green residue was chromatographed on silica gel with chloroform as the eluting solvent. Chloroform was evaporated and product triturated with methanol, again collected by filtration and vacuum dried at 70 deg C. Yield was 9 g or 45% of theoretical.

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, 6-(tert-Butyl)naphthalene-2,3-dicarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EASTMAN KODAK COMPANY; WIDZINSKI, Thomas, J.; PAWLIK, Thomas, D.; OLM, Myra, Toffolon; BOSE, Judith, A.; WO2013/55640; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 6575-05-9,Some common heterocyclic compound, 6575-05-9, name is 2,4,6-Trichlorobenzonitrile, molecular formula is C7H2Cl3N, 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.

Add 2,4,6-trichlorobenzonitrile (206 mg, 1.0 mmol) to 96% formic acid (5 niL, 96%) and water (1 mL). Add nichol/aluminum alloy (206 mg) to the mixture. Heat at 100 0C for 4 hours. Dilute with ethyl acetate and filter through Celite. Extract the filtrate with. N sodium hydroxide and saturated aqueous sodium chloride, dry (sodium sulfate), filter, and concentrate to give 2,4,6-trichlorobenzaldehyde (195 mg, 93%). 1H NMR (400 MHz, CDCl3) delta 10.36 (s, IH), 7.99 (s,lH), 7.61 (s, IH).

The synthetic route of 6575-05-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/44454; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 213598-11-9, A common heterocyclic compound, 213598-11-9, name is Methyl 3-cyano-4-isopropoxybenzoate, molecular formula is C12H13NO3, 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 mixture of methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate (27 g, 123.28 mmol) (Description 4) in methanol (150 mL) was added sodium hydroxide (5N) (27 mL, 135 mmol) and the mixture stirred at RT for 16 h. The mixture was then reduced in vacuo and acidified with hydrochloric acid (2M) (35 mL). Ethyl acetate (200 mL) was added, the layers separated and the organic layer dried over sodium sulfate and then reduced to a solid which was washed with pentane to afford the title compound (25.27 g).

The synthetic route of 213598-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BAILEY, James; KING, Nigel Paul; LIN, Xichen; REN, Feng; TAN, Kheng-Chuan; MAK, Sing Yeung; WO2011/72488; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 1813-33-8,Some common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, molecular formula is C8H3ClF3N, 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: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-4-(trifluoromethyl)benzonitrile, its application will become more common.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 330793-38-9, 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. 330793-38-9 name is 4-Bromo-2-methoxybenzonitrile, 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.

General procedure: To a stirred solution of Ar-X 9 (1.0 mmol) in THF(4.5 ml) was added dropwise a solution of i-PrMgCl in Et2O (2.0 M, 0.53 ml, 1.06 mmol) at ?40 °C under Ar and the resulting mixture was stirred at ?40 °C for 3 h and cooled to ?78 °C. To a stirred solution of dibromodifluoromethane in THF (2.46 M, 0.49 ml, 1.2 mmol) was added dropwise the prepared solution of Ar-MgCl 10 in THF via cannula at ?78 °C and the resulting mixture was gradually warmed to room temperature over 8 h. The reaction was quenched with saturated aqueous NH4Cl (10 ml) and extracted with EtOAc (10 ml x 3). The combined extracts were dried over Na2SO4. Concentration of the solvent in vacuo afforded a residue, which was purified by silica gel column chromatography and recycle GPC to give Ar-CF2Br 11.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Shiosaki, Masahiro; Inoue, Munenori; Tetrahedron Letters; vol. 55; 50; (2014); p. 6839 – 6843;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 288251-96-7, name is 2-Isobutyl-5-nitrobenzonitrile, molecular formula is C11H12N2O2, 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: 288251-96-7

(2) 5-amino-2-isobutylbenzonitrile Under an argon gas atmosphere, the compound obtained in the Example 59(1) (500 mg) was dissolved in the mixed solution of ethanol (5 ml) and ethyl acetate (5 ml), and Pt/C (sulfided) (50 mg) was added to the mixture. The atmosphere was substituted with hydrogen, and the mixture was stirred at room temperature for 6 hours. After filtration of the reaction solution on Celite, the resulting filtrate was removed under reduced pressure to obtain the target compound (447 mg) as a pale black oily substance or solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288251-96-7, its application will become more common.

Reference:
Patent; MEIJI SEIKA PHARMA CO., LTD.; YOSHIDA, Satoshi; NINOMIYA, Tomohisa; US2013/217663; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. Safety of 3-Bromo-5-fluorobenzonitrile

Step 1 [0668] 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, HCl (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 Na2SC>4 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (LXVII) (24.0 g, 117.62 mmol, 53.5% yield). NMR (CDC13, 300 MHz) ppm 3.86 (s, 2H), 7.01 (d, J=8Hz, IH), 7.12 (d, J=8Hz, IH), 7.28 (s, IH); ESIMS found C7H7BrFN mlz 203.9 (Br79M+H).

The synthetic route of 3-Bromo-5-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (254 pag.)WO2017/23980; (2017); 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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H6BrNO

General procedure: A mixture of ethyl 3-oxo-3-phenylpropanoate (2a) (1.73 mL,10.00 mmol) and allylamine [(3.75 mL, 50.00 mmol) neutralized with acetic acid (2.86 mL, 50.00 mmol)] in ethanol (10 mL) was heated to reflux for 3 h. The resulting mixture was concentrated and the residue was taken up in CH2Cl2. The organic layer was washed with 5% HCl and water, dried over MgSO4 and concentrated. Purification of the crude product by flash column chromatography (silica gel; petroleum ether/ethyl acetate95:5) afforded 3a (2.08 g, 9.00 mmol) in 90% yield as a colourless liquid. When treated with 2c, it afforded 3c instead of 3-(allylamino)-3-(2-fluorophenyl) acrylonitrile.

According to the analysis of related databases, 4592-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhai, Sheng-Xian; Dong, Hong-Ru; Chen, Zi-Bao; Hu, Yi-Ming; Dong, Heng-Shan; Tetrahedron; vol. 70; 44; (2014); p. 8405 – 8412;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

51632-29-2, name is 2-(3-Phenoxyphenyl)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. SDS of cas: 51632-29-2

3-phenoxyphenylacetonitrile was added to a 25 ml Schlenk reaction tube under a nitrogen atmosphere.(0.4 mmol), deuterated dimethylamine borane complex (4 equivalents), potassium t-butoxide (2.5 equivalents), deuterated N,N-dimethylformamide (5 ml), added to the reaction tube After the rubber stopper was placed in an oil bath, the reaction was carried out at 100 C for 18 h, and the end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography. The eluent was petroleum ether/acetic acid B. Ester (v:v=10:1),Obtaining alpha-tridemethyl-3-phenoxybenzenepropionitrile;Then, under a nitrogen atmosphere, a 25-ml two-neck round bottom flask was charged with alpha-tridemethyl-3-phenoxyphenylpropionitrile (0.2 mmol), sodium hydroxide (1.5 mmol/ml), water (8 ml). Ethanol (2ml) in round bottomThe flask was placed in a rubber bath and placed in an oil bath. The reaction was refluxed at 110 C for 5 h. The end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography. Petroleum ether / ethyl acetate (v: v = 5: 1) gave alpha-tridemethyl-3-phenoxyphenylpropionic acid, alpha-tridemethyl-fenofol.Product yield 70%, light yellow solid

The synthetic route of 51632-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Science and Technology of China; Wang Yifeng; Xia Huimin; Zhang Fenglian; (10 pag.)CN108003004; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 57381-37-0, The chemical industry reduces the impact on the environment during synthesis 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: S3 (1.5 mmol) was dissolved in NEt3 (5 mL) and degassed for 30 minutes at room temperature. Then PdCl2(PPh3)2 (0.2 mol%), CuI (0.2 mol%) and the alkyne were added to S3/NEt3 solution. The obtained dark brown suspension was stirred for 12 h at 60C. After cooling to room temperature the solvent of the reaction mixture was filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography (petroleum ether : ethyl acetate = 30:1) to provide 1t-1w (in 76-83% yield).

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, 2-Bromo-5-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Xiaodong; Deng, Guobo; Liang, Yun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2844 – 2847;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts