Tag: M.W=200-300

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

1735-53-1, Name is 4-Bromo-3-(trifluoromethyl)benzonitrile, 1735-53-1, 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.

Dissolved aryl halide (1.0 equiv) in dry DMF and subjected to degassing with a gaseous mixture of (H2 + N2) balloon for three times. Added PdCl2(PPh3)2 (10 mol %) followed by Cul (8 mol%) at r.t. Added terminal alkyne (1.0 equiv. followed by TEA. The reaction mixture stirred at 50 C or 90 C. After cooling to room temperature, the resulting solution was subjected to rotary evaporation and partitioned between EtOAc and D.I. water. Aqueous layer was extracted with EtOAc 20 mL (3x). Combined organic layers were given water, brine washes and dried over anhydrous a2S04. After evaporation of the solvent, column chromatography on silica gel afforded the desired product.

Statistics shows that 4-Bromo-3-(trifluoromethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 1735-53-1.

Reference:
Patent; LYNCH, Kevin; SANTOS, Webster; (353 pag.)WO2016/54261; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

105942-08-3, 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 105942-08-3 as follows.

Step 1: To a three-necked flask equipped with a Dean-Stark separator was charged phenol (6.17 g, 65.63 mmol), potassium carbonate (17.28 g, 125 mmol), DMF (62.5 mL) and toluene (62.5 mL) under a nitrogen atmosphere. After refluxing for 4 hours, dehydration treatment was carried out until it was confirmed that no water was produced in the system. Thereafter, toluene (50 mL) was removed using a Dean-Stark separator. After returning to room temperature, 12.5 g of 4-bromo-2-fluorobenzonitrile (62.6 mmol) was added, and the mixture was refluxed under nitrogen for 4 hr. After completion of the reaction, 100 mL of toluene was added to the solution to dilute the solution, and the solution was filtered through celite, and the obtained filtrate was washed twice with a sep. funnel, dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. The solvent is obtained to obtain a crude crystal product, which is purified by a column to obtain an intermediate.

According to the analysis of related databases, 105942-08-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Normal University; Dong Yongqiang; Xiang Xueqin; (13 pag.)CN108997299; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 179897-89-3 name is 5-Bromo-2-fluorobenzonitrile, 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. 179897-89-3

General procedure: A mixture of compound 1 (5.0 mmol), alkylamine (15.0 mmol),and K2CO3 (15.0 mmol) in DMF (10 mL) was reacted at 70e80 C for3e5 h. After the reaction was complete, the mixture was pouredinto H2O (100 mL) and extracted with ethyl acetate (100 mL 2).The organic layer was collected, washed with brine (100 mL 3),dried over anhydrous Na2SO4, and concentrated under vacuum toyield the crude product, which was purified by flash columnchromatography (0e15% ethyl acetate in petroleum ether). 4.1.1.1. 5-Bromo-2-(isobutyl(methyl)amino)-benzonitrile (2a).Yellow oil (yield: 93%); 1H NMR (400 MHz, CDCl3) d 7.54 (d, 1H,J 1.3 Hz, ArH), 7.42 (dd, 1H, J 9.1, 3.3 Hz, ArH), 6.75 (d, 1H,J 9.1 Hz, ArH), 3.19 (d, 2H, J 7.5 Hz, -NCH3CH2CH(CH3)2), 3.05 (s,3H, -NCH3CH2CH(CH3)2), 2.01 (m,1H, eNCH3CH2CH(CH3)2), 0.89 (d,6H, J 6.6 Hz, eNCH3CH2CH(CH3)2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Zhou, Haiyan; Li, Xiaolei; Li, Yuanyuan; Zhu, Xinying; Zhang, Lei; Li, Jing; European Journal of Medicinal Chemistry; vol. 186; (2020);,
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

1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, 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. 1835-65-0

General procedure: In the synthesis of Example 1 (1) The compound (4-1), except that a beta-naphthol(compound (a-1)), a 2,4,6-trimethyl-thiophenol (Compound (a-2)) It is to obtain a compound (4-2) in the same manner (yield: 68.1percent).

Statistics shows that 1835-65-0 is playing an increasingly important role. we look forward to future research findings about 3,4,5,6-Tetrafluorophthalonitrile.

Reference:
Patent; Yamada Kagaku Kogyo Corporation; Satoshi, Hayashi; Yosuke, Manabe; (47 pag.)KR2016/40133; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

52133-67-2, The chemical industry reduces the impact on the environment during synthesis 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, I believe this compound will play a more active role in future production and life.

The synthesis of target compound 3 (Scheme 1C), started with the synthesis of a reported method for compound i.?3 2-Bromo-i,i-diethoxyethane (compound 10) was reacted with ethyl2-cyanoacetate to obtain compound 1 lwhich was cyclized to compound 12 using acetamidine hydrochloride under basic conditions. Chlorination of compound 12 using POC13 provided compound 13 in 80% yield. Displacement of the chloride of compound 13 with 4-methoxy-N- methyl aniline (compound 14) and catalytic amounts of HC1 in isopropanol, provided compound1. Methylation of compound 1 with Mel under basic conditions afforded compound 3 in 85% yield. The synthesis of target compound 5 (Scheme 1C), involved N-formylation of 4-methoxy- 2-methylanline (compound 15) to afford compound 16 in 70% yield. LAH reduction of compound 16 provided substituted aniline compound 17. Displacement of the chloride of compound 13 with anilines (compounds 15 and 17) and catalytic amounts of HC1 in isopropanol provided compounds 4 and 5 (75% and 70% respectively).

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-cyano-4,4-diethoxybutyrate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DUQUESNE UNIVERSITY OF THE HOLY SPIRIT; GANGJEE, Aleem; (91 pag.)WO2016/22890; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1735-53-1, 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. 1735-53-1, name is 4-Bromo-3-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Part C. tert-butyl (7bR,11aS)-6-[4-cyano-2-(trifluoromethyl)phenyl]-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)-carboxylate. To a solution of tert-butyl (7bR,11aS)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)-carboxylate (0.135 g, 0.28 mmol) in 15 mL of DMF and 2 mL of water was added 4-bromo-3-(trifluoromethyl)benzonitrile (0.143 g, 0.57 mmol) and sodium carbonate (0.15 g, 0.1.43 mmol). The mixture was degassed with a stream of nitrogen for 20 min and then there was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (20 mg, 0.028 mmol) and the mixture was stirred at 80 C. for 16 h. The reaction was allowed to cool to ambient temperature and was diluted with ethyl acetate, washed with sat’d aqueous sodium bicarbonate and brine, dried (MgSO4), filtered through Celite and concentrated in vacuo to afford 130 mg (88%) of the title compound, which was used without purification. LRMS (ES+): 516.1 (M+H)+.

The synthetic route of 4-Bromo-3-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Robichaud, Albert J.; Fevig, John M.; Mitchell, Ian S.; Lee, Taekyu; Chen, Wenting; Cacciola, Joseph; US2004/186094; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding some certain compound to certain chemical reactions, such as: 179897-89-3, name is 5-Bromo-2-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 179897-89-3. 179897-89-3

a) 5-Bromo-2-(4-methyl-imidazol-1-yl)-benzonitrile A mixture of 5-bromo-2-fluoro-benzonitrile (25.0 g, 125 mmol), 4-methylimidazole (12.5 g, 152 mmol), potassium carbonate (34.55 g, 250 mmol) in DMSO (500 mL) was stirred at 90 C. for 16 h. Water (1.5 L) was added and the resulting suspension was stirred with ice-bath cooling for 1 h. The precipitate was filtered, washed with water (0.5 L) and dried at 50 C. over KOH. The resulting raw material (25.6 g) was dissolved in boiling Ethyl acetate (300 ml). After addition of diisopropylether (300 ml) the solution was allowed to cool to room temperature. Filtration and drying afforded the title compound (19.35 g, 59%) as a white solid. Mp 166 C.

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 5-Bromo-2-fluorobenzonitrile.

Reference:
Patent; Buettelmann, Bernd; Knust, Henner; Thomas, Andrew William; US2006/128691; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The chemical industry reduces the impact on the environment during synthesis 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, I believe this compound will play a more active role in future production and life. 1813-33-8

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate boronic acid (1.20 mmol)were dissolved in toluene/dioxane:2 N Na2CO3 (2:1:1) solution(6 ml). Tetrakis(triphenyl-phosphine)palladium(0) (0.10 mmol)and 1,10-Ferrocenediyl-bis(diphenylphosphine) (0.20 mmol) wasadded to the mixture and it was refluxed for 12 h. After cooleddown to ambient temperature, the reaction was filtered over celiteand extracted with EtOAc twice. The combined organic extractswere dried over MgSO4, filtered, and concentrated in vacuo. Theresidue was purified by flash column chromatography on silicagel using EtOAc/hexanes (1:10) eluant condition. (R-B(OH)2 =1-pentenyl boronic acid for 53, 1-cyclohexenylboronicacid for 54).

The chemical industry reduces the impact on the environment during synthesis 1813-33-8. I believe this compound will play a more active role in future production and life.

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