Tag: M.W=200-300

Synthetic Route of 877131-92-5, 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 877131-92-5 as follows.

Add hydrochloric acid (2 mL, 12M) to a solution of 2-[ 4-bromo-2(trifluoromethyl)phenyl]acetonitrile (600 mg, 2.25 mmol) in acetic acid (2 mL), the mixture is stirred at 100 C for 2 h under nitrogen. The reaction mixture is concentrated to afford title 5 compound (600 mg, 89.5%) as colorless oil. 1H NMR (400MHz, CD3Cl) () = 7.82 (d, J = 1.6 Hz, 1H), 7.67 (dd, J = 1.6, 8.4 Hz, 1H), 7.29 (s, 1H), 3.83 (s, 2H).

According to the analysis of related databases, 877131-92-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; MA, Tianwei; WU, Liang; ZHANG, Xuejun; (109 pag.)WO2019/41340; (2019); A1;,
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Reference of 1211596-75-6, 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 1211596-75-6 as follows.

Step 4: 2-(Hydroxymethyl)-6-(trifluoromethyl)benzonitrile To a solution of LiBH4 (3.3 g, 153 mmol) in THF (100 mL) was added methyl 2-cyano-3- (trifluoromethyl)benzoate (14 g, 61 mmol). The mixture was stirred at room temperature for 2 h. The mixture was concentrated in vacuo to give the crude product, which was diluted with water, and extracted with EtOAc. The organic layer was separated, dried over Na2S04, filtered, and concentrated to give the crude product 2-(hydroxymethyl)-6- (trifluoromethyl)benzonitrile (10 g, 77% yield): 1H NMR (400 MHz, CDC13) delta 7.83-7.72 (m, 3H), 5.46 (s, 2H); ES-LCMS m/z 202.1 (M+H).

According to the analysis of related databases, 1211596-75-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; KEENAN, Richard, M.; MILLER, Aaron, Bayne; QIN, Donghui; WO2013/177349; (2013); A2;,
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Application of 133541-45-4, A common heterocyclic compound, 133541-45-4, name is 4-Bromo-2,5-difluorobenzonitrile, molecular formula is C7H2BrF2N, 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 stirred suspension of 4-bromo-2,5-difluorobenzonitrile (5.0 g, 22.9 mmol) and potassium carbonate (9.5 g, 68.8 mmol) in N,N-dimethylformamide (45.9 ml) was added (S)-1 ,1 ,1 – trifluoropropanol [CAS 3539-97-7] dropwise (2.88 g, 25.2 mmol). The resulting mixture was heated at 55 “C for for 15 hours and cooled to room temperature. Water (100 ml) was added to the mixture and extracted with diethyl ether (3chi50 ml). The combined organic extracts were sequentially washed with water (2chi100 ml), brine (100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure to give an off white solid (6.93 g). The residue was purified by flash column chroamtography to give the ether as a white crystalline solid (5.90 g, 97 % purity, 80 %).LC-MS (method A): R, = 1 .29 min; MS (ESIpos): m/z = 312.0 [M+H]+1H-NMR (400 MHz, CHLOROFORM-d) delta [ppm]: 1 .51 1 (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).

The synthetic route of 133541-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; THE GENERAL HOSPITAL CORPORATION; GRADL, Stefan, Nikolaus; NGUYEN, Duy; EIS, Knut; GUENTHER, Judith; STELLFELD, Timo; JANZER, Andreas; CHRISTIAN, Sven; MUELLER, Thomas; EL SHEIKH, Sherif; ZHOU, Han, Jie; ZHAO, Changjia; SYKES, David B; FERRARA, Steven, James; LIU, Kery; HERBERT, Simon, Anthony; MERZ, Claudia; NIEHUES, Michael; NISING, Carl, Friedrich; SCHAeFER, Martina; ZIMMERMANN, Katja; KNAEBLEIN, Joerg; THEDE, Kai; FAUPEL, Thomas; (539 pag.)WO2018/77944; (2018); A2;,
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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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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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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. 925672-89-5, name is 4-Bromo-2-cyanobenzeneacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromo-2-cyanobenzeneacetonitrile

100ml of water was added to the reaction vessel, 20mmol 2-cyano-4-bromophenyl acetonitrile, 60mmol potassium phenyltrifluoroborate, 1.5mmol palladium acetylacetonate, 4mmol nitrogen ligands L-1, and p-toluenesulfonic acid monohydrate 250mmol , at 80 deg.] C under stirring for 16 hours. Anti after should be ended, the mixture was poured into ethyl acetate, sequentially with saturated NaHCO3solutionand brine, the aqueous layer was extracted with ethyl acetate, the organic layers combined (i.e., combined washedorganic layer and the extract obtained the organic layer), dried over anhydrous of Na2the SO4dried, vacuum is removed by evaporationof the solvent, the residue was purified by flash column chromatography (hexane / ethyl acetate, volume ratio of between1: 2) to give a solid target product.The yield was 61.5%,% purity of 98.7(the HPLC).

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 925672-89-5.

Reference:
Patent; Wenzhou University; CHEN, JIUXI; LIU, MIAOCHANG; CHENG, TIANXING; WANG, XIAODONG; GAO, WENXIA; HUANG, XIAOBO; WU, HUAYUE; (14 pag.)CN104557701; (2016); B;,
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Synthetic Route of 27387-23-1,Some common heterocyclic compound, 27387-23-1, name is 2-(2-Bromo-5-methoxyphenyl)acetonitrile, molecular formula is C9H8BrNO, 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.

Step 2: (2-Bromo-5-hydroxy-phenyl)-acetonitrile[00447] To (2-bromo-5-methoxy-phenyl)-acetonitrile (2.6g, 11.5mmol) in CH2Cl2 (2OmL) at O0C under N2 was added boron tribromide (IM in CH2Cl2; 25.4mL, 25.4mmol). The mixture was stirred for 15 minutes at O0C, and at room temperature overnight. After a work-up with H2O and CH2Cl2, the crude material was purified by silica gel chromatography to give the desired product as a white SoUd (1.5g).

The synthetic route of 27387-23-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMIRA PHARMACEUTICALS, INC.; WO2009/102893; (2009); A2;,
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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 99835-27-5 as follows. Computed Properties of C7H2BrCl2N

Synthesis of compound 9.3. To a solution of compound 9.2 (1.6 g, 6.37mmol, 1.0 equiv) in toluene (28 mL) was added ammonium chloride (1.7g, 31.8mmol, 5.0 equiv) at room temperature. Trimethylaluminum solution (2M in toluene) (2.29g, 31.8 mmol, 5.0 equiv) was added slowly under a nitrogen atmosphere. The mixture was heated at 110 C for 48 hrs. Upon completion, the reaction mixture was cooled to room temperature and silica was added followed by chloroform (50 mL). The resulting suspension was stirred for 30 minutes, filtered and the filter cake washed with 20% methanol in dichloromethane. The filtrate was concentrated under reduced pressure to obtain crude material, which was triturated with 10% ethyl acetate in hexane to yield compound 9.3 (1.6 g, 93%). MS (ES): m/z 269 [M+H]+.

According to the analysis of related databases, 99835-27-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
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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, name: Ethyl 3-bromo-4-cyanobenzoate

STEP 1 : A mixture of ethyl 3-bromo-4-cyanobenzoate (500 mg, 2.08 mmol), 2-methylpropan-l -amine (250 muL, 4.16 mmol), Pd2(dba)3 (96 mg, 5 mol%), Xantphos (120 mg, 10 mol%) and potassium phosphate (959 mg, 4.16 mmol) in dioxane (10 mL) was stirred for overnight at 95 0C. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated followed by column chromatography (10 % ethyl acetate in hexanes) to give ethyl 4- cyano-3-[(2-methylpropylamino)]benzoate (393 mg, 76.7 %) as a yellow solid. ‘ MS(EI) for C14H18N2O2: 247.1 (MH+).

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, Ethyl 3-bromo-4-cyanobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EXELIXIS, INC.; WO2009/55077; (2009); A1;,
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Electric Literature of 129931-47-1, 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. 129931-47-1, name is 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(i) 1-(2-Chloro-6-cyano-4-trifluoromethylphenyl)-5-bromo-4-trifluoromethyl-2-pyridone (Compound No 16 in Table II) was prepared by the reaction of 3-chloro-4-fluoro-5-cyanotrifluoromethylbenzene and 5-bromo-4-trifluoromethyl-2-pyridone. 1 H NMR delta(CDCl3) 8.10 (1H,d); 8.01 (1H,d); 7.45 (1H,s); 7.13 (1H,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, 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Imperial Chemical Industries PLC; US5109004; (1992); A;,
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