Month: March 2021

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. 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, A new synthetic method of this compound is introduced below., Formula: C10H9NO2

General procedure: A mixture of 4-methoxybenzoylacetonitrile (1.75 g, 10.0 mmol), compound 2a (3.31 g, 11.2 mmol), Et3N (4.04 g, 40.0 mmol) in t-BuOH (120 mL) was stirred at RT for 22 h. The resulting precipitate was filtered, washed with solvent t-BuOH, dried in air, then washed with some water, and dried to give white solid product 3a (2.13 g). The filtrate was evaporated and residue was extracted with EtOAc (3 ¡Á 60 mL), washed with brine, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography on silica gel with eluent (1:9 EtOAc/hexanes) to afford white solid compound 3a (0.49 g). Combined two parts of product gave 3a (2.62 g, 63%)

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:
Article; Gao, Mingzhang; Wang, Min; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 22; 11; (2012); p. 3704 – 3709;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 13388-75-5, name is 2-(3,5-Dimethoxyphenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C10H11NO2

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 synthetic route of 13388-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma, Jun; Li, Jiajun; Tian, Yu-Shun; Bioorganic and Medicinal Chemistry Letters; vol. 27; 1; (2017); p. 81 – 85;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 36282-26-5,Some common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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 48 mL pressure vessel containing 2-bromo-4-fluorobenzonitrile (1.00 g, 5.00 mmol), 2-oxazolidone (0.390 g, 4.50 mmol), K2CO3 (0.970 g, 7.0 mmol) and xantphos (0.231 g, 0.40 mmol) in dioxane (10 mL) was degassed with argon for 15 min. Pd2 dba3 (0.140 g, 0.15 mmol) was introduced and then the reaction mixture was heated at 70 C. for 18 h. The mixture was cooled, diluted with dioxane, and then filtered through Celite. The resulting mixture was concentrated in vacuo and subjected to column chromatography on silica gel with hexanes:ethyl acetate (1:1) to (3:7) gradient as the eluent to afford the title compound as a white solid (0.460 g, 50% yield): 1H NMR (400 MHz, CDCl3) ? ppm: 7.73 (1H, dd, J=5.8, 8.6 Hz), 7.43 (1H, dd, J=2.5, 9.6 Hz), 7.11 (1H, ddd, J=2.5, 7.5, 8.7 Hz), 4.60 (2H, t, J=7.1 Hz), 4.29 (2H, t, J=7.1 HJz); LCMS (+ESI, M+H+) m/z 207.

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

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

Reference of 875664-25-8, 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. 875664-25-8, name is 4-Bromo-2-phenoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Compound 5c (35.3 g, 129 mmol) was added to 130 mL EtOH, followed by the addition of 340 ml_ of 20% aqueous NaOH. The reaction was heated to reflux for 20 h. At that time the mixture was cooled to room temperature and poured into 6 N HCI. The solid was collected by vacuum filtration, dissolved in 3:1 THF-ethyl ether, and washed with brine. The organic phase was dried (MgSO4) and concentrated. The solids were dried in a vacuum oven at 60C overnight to give the desired compound 1b. MS m/z (MH+) 292.

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

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/30089; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 555-21-5, 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. 555-21-5 name is 4-Nitrophenylacetonitrile, 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.

4-Nitrophenyl acetonitrile (20 g, 123.45 mmol), tetrabutylammonium bromide (2.15 g, 6.6 mmol) and methyl iodide (58 g, 475.41 mmol) in CH2Cl2 (150 mL) were added to NaOH (13.5 g, 337.5 mmol) in water (130 mL). The reaction mixture was stirred for 20 hours at RT. The organic layer was separated, was dried over Na2SOzJ, and was evaporated to dryness. The residue was dissolved in diethylether, was filtered over celite and solvent was evaporated to obtain the title compound. Yield: 18 g (76 %); 1H NMR (CDCl3, 300 MHz): delta 8.220-8.250 (d, 2H, J=9Hz), 7.627-7.657 (d, 2H, J=9Hz), 1.750 (s, 6H).

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

Reference:
Patent; PIRAMAL LIFE SCIENCES LIMITED; KUMAR, Sanjay; VISHWAKARMA, Ram; MUNDADA, Ramswaroop; DEORE, Vijaykumar; KUMAR, Pramod; SHARMA, Somesh; WO2011/1212; (2011); 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. 332-25-2, name is 4-(Trifluoromethoxy)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 4-(Trifluoromethoxy)benzonitrile

A solution of lithium aluminium hydride in diethyl ether (1.0M, 69.4 ml) was added dropwise to a stirred solution of 4-(trifluoromethoxy)benzonitrile (6.0 g) in diethyl ether (120 ml) over 15 minutes. Water (2.66 ml), 10percent sodium hydroxide solution (2.66 ml) and water (7.98 ml) were then added successively, dropwise. The precipitated solid was filtered off and washed with diethyl ether. The filtrate and washings were combined and evaporated under reduced pressure to give 4-(trifluoromethoxy)benzyl alcohol, N.M.R. in deuteriochloroform: delta2.3 (1H,s), 4.65 (2H,s), 7.2 (2H,d), 7.35 (2H,d).

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; Imperial Chemical Industries PLC; US5006543; (1991); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 103146-25-4, 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A test tube equipped with a stopper was charged with 10 mg (0.029 m mol) of [(=T :)-4-] [4-dimethylamino-1- (4′-fluorophenyl)-1-hydroxybutyl]-3-hydroxymethylbenzonitrile, 10 mg of Novozym 435 (product of NOvozymes), 33 mg (0.29 [M MOL)] of vinyl butyrate and 1 ml of various kinds of solvents, and stirred at [30C] for 16 hours. After the reaction, converted ratios and optical purities were analyzed and E-values were calculated. The results are shown in Table 9.

The chemical industry reduces the impact on the environment during synthesis 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 19472-74-3,Some common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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 s2 in EtOH (10.0 mL) and H2O (5.0 mL) were successively added NaOH (2.94 g,73.5 mmol) and aqueous H2O2 (23 muL, 0.736 mmol) at room temperature. After the mixture washeated to reflux for 24 h, the reaction was quenched by addition of conc. HCl at 0 C. The crudemixture was extracted with EtOAc (x4) and the combined organic extracts were washed with brine,dried (Na2SO4), and concentrated in vacuo to give crude s3 (1.62 g) as pale yellow solid. Thiscrude material was used for next reaction without further purification.

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

Reference:
Article; Machida, Mizuki; Mori, Keiji; Chemistry Letters; vol. 47; 7; (2018); p. 868 – 871;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 1885-38-7, The chemical industry reduces the impact on the environment during synthesis 1885-38-7, name is (E)-Cinnamonitrile, I believe this compound will play a more active role in future production and life.

General procedure: Under a nitrogen atmosphere, a mixture of [RhCl(C2H4)2]2 (1.8 mg,0.0045 mmol) and ligand L1f (3.7 mg, 0.0099 mmol) in toluene(1 mL) was stirred at r.t. for 15 min, at which time arylboronic acid(0.60 mmol) was added, followed by cyanoalkenes (0.30 mmol),aqueous KOH (0.75 M in H2O, 0.20 mL, 0.15 mmol) and toluene(1 mL). The reaction was stirred at 80 C for 12 h, after which thereaction mixture was concentrated in vacuo and purified by silica gelflash column chromatography (petroleum ether/ethyl acetate as eluent)to give the product

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, (E)-Cinnamonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xue, Feng; Zhu, Yong; Qi, Xiaolei; Journal of Chemical Research; vol. 42; 6; (2018); p. 300 – 304;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, 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 103146-25-4, Safety of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

A test tube equipped with a stopper was charged with 10 mg (0.029 m mol) of [(=T :)-4-] [4-dimethylamino-1- (4′-fluorophenyl)-1-hydroxybutyl]-3-hydroxymethylbenzonitrile, 10 mg of Novozym 435 (product of NOvozymes), 33 mg (0.29 [M MOL)] of vinyl butyrate and 1 ml of various kinds of solvents, and stirred at [30C] for 16 hours. After the reaction, converted ratios and optical purities were analyzed and E-values were calculated. The results are shown in Table 9.

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; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts