Author: Jessica.F

Application of 555-21-5,Some common heterocyclic compound, 555-21-5, name is 4-Nitrophenylacetonitrile, molecular formula is C8H6N2O2, 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: To a screw top vial (5 mL) under N2 containing freshly distilled toluene (0.6 mL) were successively added an aromatic nitro compound (0.60 mmol), InI3 (14.9 mg, 0.030 mmol), and TMDS (318 muL, 1.80 mmol). After the vial was sealed with a cap that contained a PTFE septum, the mixture was stirred at 60 C (bath temperature), and monitored via TLC analysis. Sat. aq NaHCO3 solution (5 mL) was added to the resultant mixture, which was then extracted with EtOAc (3 × 6 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (n-hexane-EtOAc, 9:1 to 4:1) to afford the corresponding aniline derivative.

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

Reference:
Article; Sakai, Norio; Asama, Shun; Konakahara, Takeo; Ogiwara, Yohei; Synthesis; vol. 47; 20; (2015); p. 3179 – 3185;,
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. 2042-37-7, name is 2-Bromobenzonitrile, A new synthetic method of this compound is introduced below., Formula: C7H4BrN

General procedure: An aryl halide (0.5 mmol), arylboronic acid (0.75 mmol),(i-Pr)2NH (1.0 mmol), Pd/C (1.5 mol%, 16 mg), and water (1.0mL) were allowed to react at 100 C. After a certain period, the reaction mixture was added to brine (10 mL) and extracted with ethyl acetate (3 × 10 mL). The solvent was concentrated under vacuum, and the product was isolated by short chromatography on a silica-gel (200-300 mesh) column.

The synthetic route of 2042-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rao, Xiaofeng; Liu, Chun; Zhang, Yixia; Gao, Zhanming; Jin, Zilin; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 35; 3; (2014); p. 357 – 361;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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 654-70-6, Product Details of 654-70-6

Compound S-III(30.0 g, 164 mmol), 4-cyano-3-trifluoromethylaniline (33.9 g, 182 mmol)Add N, N-methylacetamide (210 mL) to the reaction flask and cool to -15 C in an ice bath.Thionyl chloride (23.0 g, 195 mmol) was added dropwise, and the reaction temperature was controlled to be -10 C to -15 C.After the addition, the mixture was stirred for 0.5 h, and raised to 40 C for 2 h. Pour the reaction solution slowly It was extracted with ethyl acetate (200 mL×3) in cold saturated sodium bicarbonate (60 mL).The organic phase was combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and filtered.Concentrate to dryness under reduced pressure to give a crude material eluting with petroleum ether and methyl tert-butyl ether Recrystallization of the solution, decolorization of activated carbon, giving a white solidS-IV 42.3 g, yield 73.1%

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; Shijiazhuang Du Zhi Pharmaceutical Technology Co., Ltd.; Fang Yu; Du Yumin; (10 pag.)CN109761778; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 19924-43-7, name is 2-(3-Methoxyphenyl)acetonitrile, 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 19924-43-7, COA of Formula: C9H9NO

Add to a 50mL single-mouth bottle with magnetic stirringCompound 22 (4 g, 27.2 mmol) and THF (40 mL)Stir and dissolve, cool to -10 C,LiHMDS (29.92 mL, 29.92 mmol, 1 M) was added dropwise and stirred for 10 minutes.Add methyl iodide(4.3g, 29.92mmol), dripping,The reaction was stirred at room temperature under a nitrogen atmosphere at 0 C overnight.The reaction was quenched by the addition of water (60 mL).Extracted with ethyl acetate (40 mL x 3), combined organic phases.Dry over anhydrous sodium sulfate, filter,concentrate,The residue was passed through a silica gel column to give a white solid3.2g,The yield was 73.5%.

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-(3-Methoxyphenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Li Huanyin; (59 pag.)CN109627263; (2019); A;,
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. 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, A new synthetic method of this compound is introduced below., Formula: C9H6N2

General procedure: A mixture of 1-aryl/alkyl-3,3-bis-methylsulfanyl-propenone (1.0 mmol), 2-cyanomethyl-benzonitrile (1 mmol, 142.0 mg), and powdered KOH (2 mmol, 112.0 mg) in dry DMSO (5 mL) was stirred at room temperature for 2 h. Completion of reaction was monitored by TLC. After completion, reaction mixture was poured onto ice-water with constant stirring and then neutralized with 10% HCl. The precipitate obtained was filtered, washed with water and dried over dry sodium sulfate. Many compounds were purified by recrystallization in dry methanol. Some compounds were purified through column chromatography using 15% ethylacetate in hexane as an eluent. Characterization data for some of the synthesized compounds are reported earlier.17

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; Singh, Surjeet; Althagafi, Ismail; Yadav, Pratik; Panwar, Rahul; Kumar, Abhinav; Pratap, Ramendra; Tetrahedron; vol. 70; 46; (2014); p. 8879 – 8884;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 185147-08-4, 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. 185147-08-4, name is 4-Fluoro-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

6.02.03.05 4-Fluoro-3-methyl-benzimidic acid ethyl ester Hydrogen chloride gas was passed through a solution of 40 g 4-fluoro-3-methylbenzonitrile in 250 mL ethanol. The reaction was stirred for 1 h at RT and for 30 min. at 40 C. Then, the solvent was evaporated, diethyl ether was added and the precipitate was filtered and dried under nitrogen. The hydrochloride was dissolved in ethanol and ammonia gas was passed through the solution. The solvent was removed and the residue was suspended in n-hexane. The suspension was filtered through silica gel and the filtrate was concentrated to yield 3.7 g of the desired product. Rt: 0.99min (method K), (M+H)+: 182

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-3-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; WELLENZOHN, Bernd; WO2013/83741; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 368-77-4, A common heterocyclic compound, 368-77-4, name is 3-(Trifluoromethyl)benzonitrile, molecular formula is C8H4F3N, 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 flask equipped with a magnetic stirrer, a nitrogen inlet, a temperature probe and a condenser was charged with the 3-(trifluoromethyl)benzonitrile (compound of formula 6) (85.5 g, 0.5 mol), followed by ethanolamine (62 ml, 1 mol), CaCI (9.0 g, 0.075 mol) and xylenes (45 mL). The reaction mixture was heated to 125 C and stirred at this temperature for 24 hr. Then the reaction mixture was allowed to cool to about 40C, and transferred with DIPE (350 mL) into an extractor containing 0.1 M KH2PO4 (600 mL). The organic phase was cut and washed with water (2×400 mL), brine (200 mL), dried over Na2S04 and filtered. The solvent was then removed under reduce pressure. The obtained crude residue was distilled using 10 cm column with Rashig rings at 90 C and 5 mbarto yield oxazoline 7 (Scheme 6) as a colorless oil (83.2 g, 77%): 1 H NMR (CDCb) delta 4.09 (t, J = 9.5 Hz, 2H), 4.47 (t, J = 9.5 Hz, 2H), 7.54 (t, J = 7.8 Hz, 1 H), 7.73 (d, J = 7.8 Hz, 1 H), 8.13 (d, J = 7.8 Hz, 1 H), 8.23 (s, 1 H).

The synthetic route of 368-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 21423-84-7, name is 2-Chloro-4-methylbenzonitrile, 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 21423-84-7, Application In Synthesis of 2-Chloro-4-methylbenzonitrile

A solution of 4-methyl-2-chlorobenzonitrile (1.51 g, 10 mmol), N-bromosuccinimide (2.14 g, 12.0 mmol) and AIBN (33 mg, 0.20 mmol) in ACN (40 ml.) was heated under reflux for 18 hours. The reaction mixture was diluted with EtOAc and washed with a saturated aqueous solution of Na2CO3 and brine. The organic layer was dried (MgSO4) and concentrated under vacuum. The residue was treated with sarcosine te/f-butyl ester hydrochloride (1.44 g, 7.92 mmol) and K2CO3 (2.74 g, 19.8 mmol) in ACN (10 ml_). The mixture was heated at 10O0C for 2 hours. The solvent was evaporated under vacuum. The residue was dissolved in a mixture of DCM and water and then poured through a hydrophobic frit. The solvent was evaporated under vacuum. The residue was purified by flash chromatography (silica, /so-hexane/Et2O) to afford the title compound (1.95 g, quantitative). 1H NMR (CDCI3, 400 MHz) delta 7.61 (1 H, d, J=8.0 Hz), 7.57 (1 H, s), 7.36 (1 H, m), 3.73 (2H, s), 3.21 (2H, s), 2.36 (3H, s), 1.48 (9H, s).

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

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; MONTAGNE, Cyril; SAUER, Wolfgang; CROSIGNANI, Stefano; BOMBRUN, Agnes; WO2010/112461; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 36282-26-5, 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 36282-26-5 as follows.

A mixture of 4-fluoro-2-bromobenzonitrile (10.0 g, 50.0 mmol), potassium acetate (9.82 g, 100 MMOL), bis (pinacolato) diboron (14.0 g, 55.0 mmol) and dichloro [L, L’-BIS (diphenylphosphino) FERROCENE] PALLADIUM (II) CH2CL2 adduct (0.82 g, 1.0 mmol) in 1,4-dioxane (150 ml) and dimethylsulfoxide (3 ml) was degassed with nitrogen for 1 h then heated at 85C for 20 h. The reaction was cooled to ambient temperature and then concentrated in vacuo. The residue was stirred with 2 N sodium hydroxide (250 ml) for 10 min then filtered. The filtrate was extracted with diethyl ether (300 ml) and the organics discarded. The aqueous component was cooled to 0C then treated with 5 N hydrochloric acid, added dropwise over 15 min until the pH was 8. The aqueous phase was extracted with EtOAc (2 x 200 ML), THE COMBINED organics were dried over anhydrous sodium sulfate, filtered and evaporated to afford the title compound (10.9 g, 88%) as a pale brown solid: BA (360 MHz, CDCL3) 1.38 (12 H, s), 7.15-7. 25 (1 H, M), 7.53-7. 60 (1 H, m), 7.67-7. 75 (1 H, m).

According to the analysis of related databases, 36282-26-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/65388; (2004); 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. 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-2-methylbenzonitrile

To a solution of 4-bromo-2-methylbenzonitrile (2.0 g, 10.2 mmol) in THF (100 ml) at -78C under a nitrogen atmosphere was added dropwise a 2.5 M solution of n-butyl lithium (4.48 ml, 11.2 mmol). The mixture was stirred at -78C for 1h and then poured onto solid carbon dioxide (5 g) in THF (50 ml). The mixture was allowed to warm to room temperature. Water was added (200 ml) and the mixture was extracted with diethyl ether (3 times). The aqueous layer was acidified by addition of concentrated HCl and extracted with chloroform (3 times). The combined chloroform extracts were washed with water, dried over MgSO4, and concentrated in vacuo to give a white solid identified as 4-cyano-3-methylbenzoic acid (1.2 g, 73%).

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; Ferring B.V.; EP1449844; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts