Month: July 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. 64248-62-0, name is 3,4-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,4-Difluorobenzonitrile

In N, N-dimethylformamide (DMF, 40 mL)(R) -2- (4-hydroxyphenoxy) propionic acid (3.03 g, 0.02 mol) was added,Potassium carbonate (5.52 g, 0.04 mol) was added in portions,Heating to 70 C to 80 C,Continuous stirring 1h,(2.38 g, 0.02 mol) of 3,4-difluorobenzonitrile was added in portions,Continue to stir the reaction 6 ~ 7h.Cooled to room temperature,Poured into ice water (250 mL)Slowly add dilute hydrochloric acid,Adjusted to pH 4 to 5,Filter,Washed,(R) -2- [4- (4-cyano-2-fluorophenoxy) phenoxy] propionic acid as a gray solid in (R) -2- [4- (4-cyanide) Yl-2-fluorophenoxy) phenoxy] propionic acid3.26g,Yield 65.7%.

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; China Three Gorges University; Liu, Qixing; Zhou, Haifeng; Zhu, Rui; Chen, Lei; (9 pag.)CN106632007; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 17216-62-5, name is Diethyl 2-(2-cyanoethyl)malonate, 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 17216-62-5, category: nitriles-buliding-blocks

(a) 4-Cyano-2(R,S)-alpha-naphthylmethylbutyric acid 2.13 g of 2-cyanoethylmalonic acid diethyl ester are added to a suspension of 0.48 g of sodium hydride dispersion in 25 ml of DMF. The reaction mixture is stirred for 2 hours at 80 and then, at room temperature, 1.77 g of alpha-chloromethylnaphthalene in 5 ml of DMF are added. The mixture is further stirred for 16 hours at 50 and then concentrated by evaporation. The residue is dissolved in ethyl acetate, washed with 0.1N hydrochloric acid and water, dried over sodium sulphate and concentrated by evaporation, leaving 2-cyanoethyl-alpha-naphthylmethylmalonic acid diethyl ester.

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, Diethyl 2-(2-cyanoethyl)malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ciba-Geigy Corporation; US4727060; (1988); A;,
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-pyrrolidinone (0.46 mL, 6.00 mmol), Cs2CO3 (2.28 g, 7.0 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (xantphos) (0.231 g, 0.40 mmol) in dioxane (6 mL) was degassed with argon for 15 min. Pd2dba3 was introduced and the reaction mixture heated at 105 C. for 48 h. The mixture was cooled, diluted with ethyl acetate or 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 (3:7) gradient as the eluent to afford the title compound as a white solid (0.887 g, 87% yield): 1H NMR (400 MHz, CDCl3) delta ppm: 7.69 (1H, dd, J=5.8, 8.6 Hz), 7.22 (1H, dd, J=2.5, 9.6 Hz), 7.07 (1H, ddd, J=2.5, 7.6, 8.6 Hz), 3.96 (2H, t,. J=7.0 Hz), 2.62 (2H, t, J=8.1 Hz), 2.30-2.22 (2H, m); LCMS (+ESI, M+H+) m/z 205.

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; Bristol-Myers Squibb Company; US2007/111984; (2007); 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. 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Methyl-3-oxopentanenitrile

General procedure: A mixture of 4-methyl-3-oxopentanenitrile 10i or 10ii (1.5eq), aldehyde 6(a-m) (1.0 eq), urea (1.5 eq) and CuCl (0.01eq) in MeOH containing concentrated H2SO4 (0.62 eq) wasstirred at reflux temperature for 3-5 days. After the reactionwas deemed complete by TLC, methanol was removed byconcentration in vacuo. The precipitated solid was extractedin dichloromethane. The dichloromethane layer was washedwithwater twice so as to removewater soluble impurities. Theorganic layerwas concentrated again to dryness in vacuo. Thecrude residue was purified by silica gel column chromatographyusing ethyl acetate: hexanes to give pyrimidine compound11(a-m).

According to the analysis of related databases, 29509-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pachore, Sharad S; Ambhaikar, Narendra B; Siddaiah, Vidavalur; Khobare, Sandip R; Kumar, Sarvesh; Dahanukar, Vilas H; Kumar, U K Syam; Journal of Chemical Sciences; vol. 130; 6; (2018);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 57381-34-7, 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. 57381-34-7, name is 5-Chloro-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred 00C solution of 1,1,1,3,3,3-Hexamethyldisilazane (63 mL, 0.3 mol) in dry diethyl ether was added dropwise n-Butyl lithium (2M in hexanes, 150 mL, 0.3 mol). A white suspension formed, to which was added 2-Fluoro-5-chlorobenzonitrile (21.0 g, 0.14 mol) over 5 min. The resultant orange mixture was allowed to warm to r.t. and stirred for 2h. The mixture was cooled to 00C and the reaction quenched by the addition of 3M HCl (aq.) (240 mL). The mixture was stirred for 0.5h before water (600 mL) was added. The purple organic layer was discarded and the aqueous layer basified to pH 14 with satd. NaOH (aq.). The aqueous layer was extracted with CHCI3 (5×100 mL) and the organic extracts dried over Na2SO4. Evaporation yielded the desired product as a yellow solid (16.2g, 73% yield).

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

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2008/40778; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 6621-59-6, 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. 6621-59-6, name is 6-Bromohexanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

Step a: A 3% solution of the respective iminoalditol in dry DMF was stirred with omega-bromohexanoic nitrile (2 equiv.) in the presence OfNa2CO3 (1.3 equiv.) at 40 0C for 72 h. Removal of the solvent and chromatographic purification (CHClj/MeOH 1 :1) gave the respective reaction products in yields ranging between 45 and 90 %.

The chemical industry reduces the impact on the environment during synthesis 6-Bromohexanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; TECHNISCHE UNIVERSITAeT GRAZ; WO2006/100586; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 362527-61-5, name is Ethyl 3-bromo-4-cyanobenzoate, 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 362527-61-5, Application In Synthesis of Ethyl 3-bromo-4-cyanobenzoate

STEP 1 : A mixture of ethyl 3-bromo-4-cyanobenzoate (500 mg, 1.97 mmol), XANTPHOS (228 mg, 0.39 mmol), cesium carbonate (1.282 g, 3.94 mmol), cyclopentylamine (233 mg, 2.75 mmol), and tris(dibenzylideneacetone)dipalladium (180 mg, 0.20 mmol) in dioxane (5 mL) was stirred at 1000C for 17 h. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (50 mL), the organic layer washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated. Column chromatography on silica (hexanes: ethyl acetate 9: 1) afforded ethyl 4-cyano-3-(cyclopentylamino)benzoate (366 mg, 72% yield) as a brown oil. 1H NMR (400 MHz, CDCl3): 7.43 (m, 2H), 7.35 (m, IH), 7.27 (m, IH), 4.62 (d, IH), 4.38 (q, 2H), 3.93 (m, IH), 2.10 (m, 2H), 1.78 (m, 2H), 1.67 (m, 2H), 1.53 (m, 2H),1.39 (t, 3H). MS (EI) for Ci5H18N2O2: 259 (MH+).

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

Reference:
Patent; EXELIXIS, INC.; WO2009/55077; (2009); A1;,
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 3598-13-8 as follows. Formula: C8H6ClNO

Starting Material 7: (6-Nitro-2-phenyl-benzoxazole-7-yl)-acetonitrile STR24 To a stirred suspension of potassium tert-butoxide (701 mg, 6.25 mmol) in DMF (6 mL) was added a solution of 6-nitro-2-phenyl-benzoxazole (500 mg, 2.08 mmol)(Starting Material 3) and 4-chlorophenoxyacetonitrile (366 mg, 2.19 mmol) (Aldrich) in DMF (20 mL) at -30 C. The mixture was then stirred at this temperature for 3 h and neutralized with aqueous 1N hydrochloric acid solution at 0 C. The aqueous layer was extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to give a yellow solid. The crude product was purified by silica gel chromatography. (Yield 520 mg, 90%).

According to the analysis of related databases, 3598-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US6153634; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 75279-53-7, name is 4-Chloro-2-fluorobenzeneacetonitrile, 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 75279-53-7, Application In Synthesis of 4-Chloro-2-fluorobenzeneacetonitrile

To a solution of 4-chloro-2-fluoro-benzyl cyanide (Oakwood) (1.70 g, 10.0 mmol) and 3,3-dimethyl-butyraldehyde (Aldrich) (1.0 g, 10.0 mmol) in iPrOH (20 mL) was added 2 N NaOH (2.0 mL) dropwise at rt and the reaction mixture was stirred at rt overnight. The reaction mixture was diluted with EtOAc and the organic layer was separated, washed with water, brine, dried over Na2SO4 and concentrated. The residue was dried overnight in vacuum to give (Z)-2-(4-chloro-2-fluoro-phenyl)-5,5-dimethyl-hex-2-enenitrile (2.52 g, 100%) as a colorless oil which was used in the next step without further purification.

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-Chloro-2-fluorobenzeneacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Liu, Jin-Jun; Morgan Ross, Tina; Zhang, Zhuming; US2011/86854; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 185147-07-3,Some common heterocyclic compound, 185147-07-3, name is 2-Fluoro-3-methylbenzonitrile, molecular formula is C8H6FN, 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.

2-fluoro-3-methylbenzonitrile (18 g, 133 mmol) was added to a solution of potassium nitrate (13.5 g, 133 mmol) in sulfuric acid (250 mL) cooled at 0C, the mixture was allowed to stir at room temperature for 40 minutes. The reaction mixture was poured into ice water and the pale yellow precipitate was filtered off and dried in the vacuum oven yielding crude 2-fluoro-3- methyl-5-nitro-benzonitrile (18 g). Crude 2-fluoro-3-methyl-5-nitro-benzonitrile (18 g) was stirred in MeOH (210 mL) and water (70 mL). Fe powder (16.7 g) and HC1 (36 mL, 5 equiv) were added and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then filtered through celite and after removal of organic solvent, the mixture was adjusted to pH 9 with saturated solution of sodium carbonate and extracted with CH2C12 twice. The combined organic layers were dried over sodium sulfate and evaporated to dryness to provide a yellow oil. The crude product was purified by column chromatography to provide 5-amino-2- fluoro-3-methyl-benzonitrile (5.1 g) as a pale yellow solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-3-methylbenzonitrile, its application will become more common.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2014/184365; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts