Author: Jessica.F

These common heterocyclic compound, 64248-63-1, name is 3,5-Difluorobenzonitrile, 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. SDS of cas: 64248-63-1

Preparation 33 3-Fluoro-5-methoxybenzonitrile Sodium methoxide (1.50 ml of a 4.5M solution in methanol, 7.10 mmol) was added dropwise to a stirred solution of 3,5-difluorobenzonitrile (1.00 g, 7.10 mmol) in N,N-dimethylformamide (36 ml) at 0 C. under nitrogen. The reaction was allowed to warm to room temperature and stirred for 14 hours. The reaction was diluted with ether (40 ml), washed with water (3*100 ml) and brine (100 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluding with cyclohexane:ethyl acetate (95:5, by volume) to provide the title compound (418 mg) as a yellow oil. 1H-NMR (400 MHz, CDCl3): delta=3.84 (s, 3H), 6.82 (dd, 1H), 6.95 (dd, 1H), 6.96 (s, 1H).

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

Reference:
Patent; Jones, Lyn Howard; Mowbray, Charles Eric; Price, David Anthony; Selby, Matthew Duncan; Stupple, Paul Anthony; US2003/100554; (2003); A1;,
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Electric Literature of 6283-71-2, These common heterocyclic compound, 6283-71-2, name is Dimethyl 2-cyanosuccinate, 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.

Sodium nitrite (1.32 g, 19.1 mmol) was added carefully to sulphuric acid (concentrated, 6.8 ml), whilst cooling the solution to 0° C. The solution was heated to 60° C. for 30 min, allowed to cool and then diluted with acetic acid (12 ml). To the solution was added Preparation 182 (5.0 mg, 17.4 mmol) in acetic acid (11 ml) and the reaction mixture was heated at 55° C. for 1 h. To a solution of Preparation 248 (3.09 g, 18.1 mmol) in acetic acid (24 ml) and water (36 ml) was added dropwise the solution of the diazonium salt, followed by sodium acetate (24.2 g) in water (42 ml). The reaction mixture was then stirred at room temperature for 30 min. The reaction mixture was poured into ice/water (200 ml) and the mixture was extracted with dichloromethane (4.x.60 ml). The combined extracts were then washed with ammonium hydroxide (48 ml), dried and concentrated in vacuo. To a solution of sodium methoxide (25 wt.percent, 11.5 ml, 50.1 mmol) in methanol (450 ml) was added dropwise a solution of the residue in methanol (100 ml). The reaction mixture was then stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and to the residue was added water. This solution was adjusted to pH 1 by addition of hydrochloric acid (4 N) and the mixture was extracted with dichloromethane (3.x.100 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography, eluting with hexane/ethyl acetate [3: 1]. The appropriate fractions were combined and concentrated to give the titled compound (4.5 g). Experimental MH+ 379.8; expected 380.0

The synthetic route of 6283-71-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Billen, Denis; Boyle, Jessica; Critcher, Douglas James; Gethin, David Morris; Hall, Kim Thomas; Kyne, Graham Michael; US2006/287365; (2006); A1;,
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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 57775-06-1 as follows. name: 2-(2-Bromophenyl)-2-methylpropanenitrile

General procedure: To a screw-capped vial (25 mL) were added NaOH (400 mg, 10 mmol), tert-butanol (tBuOH, 10 mL) and 3a (1.12 g, 5 mmol). The vial was sealed with cap and allowed to stir at 100 °C. The reaction was monitored by TLC every hour until the complete consumption of 3a. After total conversion of 3a, the reaction was diluted with CH2Cl2, filtered through a thin Celite pad to remove salt, and concentrated in vacuo. The residue was isolated through a short flash column chromatography by using ethyl acetate as eluent to give the pure compound 1a in 92percent isolated yield; White solid, mp: 73?74 °C; IR (KBr): 3472, 2977, 2932, 1669, 1605, 1468, 1427, 1390, 1360, 1022, 756 cm-1; 1H NMR (600 MHz, CDCl3): delta 7.60 (dd, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H), 7.49 (dd, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H), 7.34 (td, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H), 7.14 (td, J1 = 7.8 Hz, J2 = 1.8 Hz, 1H), 5.72 (br, 1H), 5.23 (br, 1H), 1.65 (s, 6H); 13C NMR (150 MHz, CDCl3): delta 179.0, 143.0, 134.8, 128.6, 127.7, 127.6, 124.1, 48.3, 26.4; HRMS: C10H12BrNO calculated 241.0102, found 241.0098; Registry Number: [173026-22-7]. Compounds 1b?1q were obtained according to this procedure. The synthetic methods for all the nitrile compounds 3 were prepared according to our previous report.2

According to the analysis of related databases, 57775-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jhan, Yu-Huei; Kang, Ting-Wei; Hsieh, Jen-Chieh; Tetrahedron Letters; vol. 54; 9; (2013); p. 1155 – 1159;,
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Related Products of 3100-67-2, 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. 3100-67-2, name is 1-Amino-2-naphthonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The [Reaction Scheme 1-1 [Intermediate a-1] 50.0 g (297 mmol), 500 mL of dimethylformamide was stirred obtained from. Then N-bromo-succinimide 55.56 g (312 mmol) was added slowly to the reactor. After raising to room temperature and stirred for 4 hours. When the reaction is completed, distilled water was added dropwise thereto at room temperature saenggimyeon brown crystals Crystals were filtered and separated by column chromatography with [intermediate 1-b] compound 68 g. (Yield: 92.6%).

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, 1-Amino-2-naphthonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SFC CO., LTD.; PARK, PU BAE; PARK, JI HEE; SHIN, PONG KI; YOO, JUNG HO; YANG, BYUNG SOON; LEE, SE JIN; (61 pag.)KR2015/111106; (2015); A;,
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Adding a certain compound to certain chemical reactions, such as: 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, 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 66389-80-8, HPLC of Formula: C13H16N2O2

tert- Butyl (4-cyanobenzyl)carbamate (1 g, 4mmol) was suspended in 10 mL ethanol and heated to 80C. To the solution was added 10 mL of aqueous hydroxylamine and the mixture was heated for 3 hours and allowed to cool to room temperature and stirred overnight. After concentration the residue was concentrated to half volume, and product extracted with ethyl acetate (3 x 15 ml). The combined organic layer was washed with brine (15 mL), dried over anhydrous sodium sulfate, and the solvent was evaporated to dryness to yield white solid (890 mg) which was taken to the next step. Mass Spec, MH+ = 266

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

Reference:
Patent; TOSK, INC.; LENNEK, Annie L.; YANOFSKY, Stephen D.; FRENZEL, Brian D.; UNGASHE, Solomon B.; GARLAND, William A.; LIAW, Philip; (105 pag.)WO2020/33413; (2020); A2;,
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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. 4387-32-0, name is 2-Chloro-5-methylbenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-5-methylbenzonitrile

To a solution of 2-chloro-5-methyl-benzonitrile (9.0 g, 59.4 mmol) in anhydrous THF (90 mL) at 0 C was added BH3-THF (1.0 M, 178 mL, 178 mmol) dropwise under a nitrogenatmosphere. The mixture was stirred at room temperature for 12 h. The reaction was quenched with 2N HC1 (110 mL) at 0 C and then heated to 70 C for 1 h. After cooling the reaction to room temperature, the solution was washed with DCM (150 mL). The aqueous phase was basified with iN NaOH to pH 8 and then extracted with DCM (150 mL x 3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give thetitle compound (5.8 g, 63%) as yellow oil. ?HNMR (400 IVIFIz, CDC13) 7.22 (d, J 8.0 Hz,1H), 7.17 (s, 1H), 6.99 (d, J= 8.0 Hz, 1H), 3.88 (s, 2H), 2.32 (s, 3H).

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; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
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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 133541-45-4 as follows. Computed Properties of C7H2BrF2N

To a stirred suspension of 4-bromo-2,5-difluorobenzonitrile (91 g, 417 mmol) and potassium carbonate (173 g, 1.25 mol) in N,N-dimethylformamide (910 ml) was added (S)-l,l,l- trifluoropropanol [CAS 3539-97-7] dropwise (52.4 g, 460 mmol). The resulting mixture was heated at 70 C for for 15 hours and cooled to room temperature. The reaction was concentrated and the residue was diluted with water. The aqueous solution was extracted with DCM (3x). The combined organic washes were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give an oil (136.6 g). The residue was triturated with a mixture of hexanes and toluene (9:1, 200 mL) to give the desired product as a white solid (90.3 g, 93% purity, 64% yield). LC-MS (Method A): R, = 1.29 min; MS (ESIpos): m/z = 312.0 [M+H]+. 1H-NMR (400 MHz, CHLOROFORM-d) d [ppm] : 1.511 (4.41), 1.531 (15.64), 1.533 (16.00), 1.548 (15.84), 1.550 (15.83), 4.566 (1.08), 4.581 (2.68), 4.597 (3.18), 4.612 (2.62), 4.626 (1.01), 7.194 (5.27), 7.207 (7.60), 7.220 (7.57).

According to the analysis of related databases, 133541-45-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; JANZER, Andreas; POLITZ, Oliver; EHEIM, Ashley, Lakner; (87 pag.)WO2019/197269; (2019); A1;,
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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. 508203-48-3, name is 2,3-Difluoro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 508203-48-3

To a suspension of 2,3-difluoro-4-methylbenzonitrile (5.0 g, 32.6 mmcl) in ethanol (111 mL) at25C was added hydroxylamine hydrochloride (4.5 g, 65.3 mmol). The reaction mixture was heated at80C for 2 hours. After cooling to room temperature, the volatiles were removed under reduced pressurethus affording a white solid that was used in the next transformation without purification.1H NMR (400 MHz, CDCI3) oe ppm: 7.30 (m, 1H), 6.95 (m, 1H), 6.50 (brs, 1H), 5.05 (brs, 2H),2.30 (s, 3H).

According to the analysis of related databases, 508203-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; BEAUDEGNIES, Renaud; POULIOT, Martin; HAAS, Ulrich, Johannes; (161 pag.)WO2018/177894; (2018); A1;,
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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. 13726-21-1, name is 2-(4-Chloro-3-methoxyphenyl)acetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(4-Chloro-3-methoxyphenyl)acetonitrile

(4-Chloro-3-hydroxy-phenyl)acetonitrile BBr3 (17 g, 66 mmol) was slowly added to a solution of 2-(4-chloro-3-methoxyphenyl)acetonitrile (12 g, 66 mmol) in dichloromethane (120 mL) at -78 C. under N2. The reaction temperature was slowly increased to room temperature. The reaction mixture was stirred overnight and then poured into ice and water. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (40 mL*3). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under vacuum to give (4-chloro-3-hydroxy-phenyl)-acetonitrile (9.3 g, 85%). 1H NMR (300 MHz, CDCl3) delta 7.34 (d, J=8.4 Hz, 1H), 7.02 (d, J=2.1 Hz, 1H), 6.87 (dd, J=2.1, 8.4 Hz, 1H), 5.15 (brs, 1H), 3.72 (s, 2H).

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; Vertex Pharmaceuticals Incorported; US2011/98311; (2011); A1;,
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Electric Literature of 191014-55-8, A common heterocyclic compound, 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, molecular formula is C8H6FNO, 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 solution of 1 g of 4-fluoro-2-methoxy-benzonitrile in 15 mL of dichloroethane was added 1.1 g of aluminum trichloride. The resulting mixture was refluxed for 1 day then poured slowly into water and extracted with ethyl acetate. The organic extracts were washed twice with 10% aqueous solution of sodium hydroxide. The combined basic layers were washed twice with ethyl acetate, acidified with concentrated aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic extracts were washed with water, with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 0.78 g of 4-fluoro-2-hydroxy-benzonitrile as a white solid.C7H4FNO (137.11), MS (ESI): 138.17 (M+H+).

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2008/261979; (2008); A1;,
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