Month: February 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. 21423-81-4, name is 3-Chloro-4-methylbenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Chloro-4-methylbenzonitrile

A mixture of 3-chloro-4-methylbenzonitrile (4.8 g), Lambda/-bromosuccinimide (5.5 g), dibenzoyl peroxide (0.43 g) and carbon tetrachloride (30 mL) was heated a reflux for 2 hours. The mixture was cooled to room temperature, filtered and washed with dichloromethane. The filtrated was washed with water, dried over sodium sulfate and the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 19:1 by volume) gave title compound, 4.1 g.1H NMR (CDCI3): delta 4.55 (s, 2H), 7.55 (m, 2H), 7.70 (m, 1H).

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; ARGENTA DISCOVERY LTD.; WO2007/36743; (2007); A2;,
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. 97165-77-0, name is 3,5-Dibromobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 3,5-Dibromobenzonitrile

To a round bottom flask was added 20.0 g (77 mmol) of 3,5-dibromobenzonitrile and 13.2 g (77 mmol) of 1-naphthaleneboronic acid,1.8 g (2 mmol) of tetrakistriphenylphosphine palladium {Pd (PPh3) 4}21.2 g (153 mmol) of potassium carbonate,30 mL of water,100 ml of toluene and 100 ml of tetrahydrofuran were added and the mixture was refluxed for 12 hours.After completion of the reaction, the reaction product was separated, and the organic layer was concentrated under reduced pressure.Hexane, and dried to obtain 13.1 g of a white solid having a yield of 55.5%.

The synthetic route of 97165-77-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC Ltd.; Ryu Se-jin; Sim So-yeong; Lee Sang-hae; (39 pag.)KR101964677; (2019); B1;,
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. 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Chloro-4-(trifluoromethyl)benzonitrile

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

According to the analysis of related databases, 1813-33-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 38487-86-4, 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. 38487-86-4 name is 2-Amino-4-chlorobenzonitrile, 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.

To a suspension of anhydrous AlCl3 (570 mg, 4.27 mmol) and freshly sublimed 2-amino-4-chlorobenzonitrile (618 mg, 4.05 mmol) in 1,2-dichloroethane (6 mL) was added dropwise a solution of enone 7 (R9 = i-Pr) (440 mg, 2.50 mmol) in 1,2-dichloroethane (27 mL). The reaction mixture was stirred under reflux for 14 h, allowed to cool to room temperature, diluted with water (35 mL) and THF (35 mL), made basic by addition of 5 N NaOH (20 mL), and stirred at room temperature for 30 min. The organic solvents were removed under reduced pressure, and the residue was filtered. The brown solid residue (698 mg) was subjected to column chromatography [silica gel (50 g), CH2Cl2/MeOH/25% aqueous NH4OH mixtures as eluent]. On elution with CH2Cl2/MeOH/25% aqueous NH4OH 98:2:0.5, huprine 8 (335 mg, 48% yield) was obtained as a beige solid.A solution of huprine 8 (335 mg, 1.07 mmol) in CH2Cl2 (15 mL) was filtered through a polytetrafluoroethylene (PTFE) 0.45 mum filter, treated with 1.81 N methanolic solution of HCl (1.24 mL, 2.24 mmol), and the resulting solution was evaporated under reduced pressure. After recrystallization of the resulting solid residue from AcOEt/MeOH 8:1 (9 mL), 8¡¤HCl (274 mg) was obtained as a beige solid, mp 218-219 C (AcOEt/MeOH 8:1). IR (KBr) nu 3500-2500 (max at 3476, 3322, 3172, 2956, 2926, 2892, 2821, C-H, N-H, and N+-H st), 1644, 1609, 1576, and 1557 (ar-C-C and ar-C-N st) cm-1; 1H NMR (500 MHz, CD3OD) delta 0.80 (d, J = 7.0 Hz, 3H) and 0.84 (d, J = 7.0 Hz, 3H) [9-CH(CH3)2], 1.92 (dm, J = 12.0 Hz, 1H, 13-Hsyn), 1.97-2.06 [complex signal, 2H, 13-Hanti and 9-CH(CH3)2], 2.09 (d, J = 17.0 Hz, 1H, 10-Hendo), 2.45 (dd, J = 17.0 Hz, J’ = 5.0 Hz, 1H, 10-Hexo), 2.70 (m, 1H, 7-H), 2.82 (ddd, J = 17.5 Hz, J’ = J = 2.0 Hz, 1H, 6-Hendo), 3.05 (dd, J = 17.5 Hz, J’ = 5.5 Hz, 1H, 6-Hexo), 3.34 (m, 1H, 11-H), 4.86 (s, NH2 and NH+), 5.52 (dm, J = 5.0 Hz, 1H, 8-H), 7.30 (dd, J = 8.5 Hz, J’ = 2.0 Hz, 1H, 2-H), 7.66 (d, J = 2.0 Hz, 1H, 4-H), 8.06 (d, J = 8.5 Hz, 1H, 1-H); 13C NMR (75.4 MHz, CD3OD) delta 21.4 (CH3) and 21.9 (CH3) [9-CH(CH3)2], 28.2 (CH, C11), 29.2 (CH, C7), 30.4 (CH2, C13), 32.3 (CH2, C10), 35.9 [CH, 9-CH(CH3)2], 39.5 (CH2, C6), 115.5 (C) and 116.6 (C) (C11a and C12a), 122.9 (CH, C4), 124.6 (CH), 124.9 (CH), and 125.4 (CH) (C1, C2, and C8), 136.6 (C, C4a), 143.9 (C) and 145.9 (C) (C3 and C9), 151.4 (C) and 157.8 (C) (C5a and C12). Anal. Calcd for C19H21ClN2¡¤HCl¡¤1/3H2O (355.25): C, 64.24; H, 6.43; N, 7.89; Cl, 19.96. Found: C, 64.09; H, 6.45; N, 7.64; Cl, 19.70.

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

Reference:
Article; Defaux, Julien; Sala, Marta; Formosa, Xavier; Galdeano, Carles; Taylor, Martin C.; Alobaid, Waleed A.A.; Kelly, John M.; Wright, Colin W.; Camps, Pelayo; Munoz-Torrero, Diego; Bioorganic and Medicinal Chemistry; vol. 19; 5; (2011); p. 1702 – 1707;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, 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. Recommanded Product: 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

Experiment 7: The general procedure of Experiment 2 was applied. No acetic acid was present in the system. The experiment was carried out with a small amount of water (0.0 IV) An exemplary batch gave molar yield: 32.5%; enantiomeric purity: 98.7% S. Experiment 8: The general procedure of Experiment 2 was applied. No acetic acid was present in the system. The experiment was carried out with a higher amount of water (0.05V) Exemplary batches gave: Molar yield: 34.7%; enantiomeric purity: 99.0% S.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103146-25-4, its application will become more common.

Reference:
Patent; H. LUNDBECK A/S; WO2009/33488; (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 939-79-7 as follows. HPLC of Formula: C8H6N2O2

(2) 4-Bromomethyl-3-nitrobenzonitrile A solution of 4-methyl-3-nitrobenzonitrile (30 g), N-bromosuccinimide (37 g) and azobisisobutyronitrile (3.1 g) in carbon tetrachloride (300 ml) was refluxed under heating for 8 hr. To the reaction mixture was added water (100 ml) and the mixture was extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate_hexane=1:4) and recrystallized from ethyl acetate-hexane to give the title compound (23.7 g) as pale-yellow crystals, m.p.=85-89 C. 1H-NMR(DMSO-d6)delta: 4.96(2H, s), 7.97(1H, d, J=7.9 Hz), 8.22(1H, dd, J=1.3, 7.9 Hz), 8.61(1H, d, J=1.3 Hz); IR(KBr): 3082, 2235, 1614, 1530 cm-1; MS(EI): 241(M+); Elemental analysis: Calculated: C; 39.86, H; 2.09, N; 11.62; Found: C; 40.64, H; 2.15, N; 11.85.

According to the analysis of related databases, 939-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Pharma Corporation; US6455528; (2002); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 51632-29-2, 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 51632-29-2 as follows.

3-phenoxyphenylacetonitrile was added to a 25 ml Schlenk reaction tube under a nitrogen atmosphere.(0.4 mmol), dimethylamine borane complex (1 equivalent), potassium t-butoxide (1.5 eq.), deuterated N,N-dimethylformamide (2 ml), rubber stopper on the reaction tube After being placed in an oil bath, the reaction was carried out at 80 C for 7 h, and the end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography, and the eluent was petroleum ether / ethyl acetate ( v: v = 10: 1), obtaining alpha-monodecylmethyl-3-phenoxybenzenepropionitrile;Then, under a nitrogen atmosphere, a 25 ml two-neck round bottom flask was charged with alpha-monodeuteromethyl-3-phenoxyphenylpropanenitrile (0.2 mmol), sodium hydroxide (1.5 mmol/ml), water (8 ml). Ethanol (2ml), burned in a round bottomThe bottle was placed in a rubber bath and placed in an oil bath. The reaction was refluxed at 110 C for 5 h. The end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography. Petroleum ether / ethyl acetate (v: v = 5: 1) gave alpha-monodecylmethyl-3-phenoxyphenylpropionic acid, i.e., alpha-monodecylmethyl-fenofol.Product yield 80%, light yellow solid

According to the analysis of related databases, 51632-29-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; University of Science and Technology of China; Wang Yifeng; Xia Huimin; Zhang Fenglian; (10 pag.)CN108003004; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 4553-07-5, The chemical industry reduces the impact on the environment during synthesis 4553-07-5, name is Ethyl 2-cyano-2-phenylacetate, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of methyleneindolinone (0.1 mmol, 1 equiv), and isocyanide (0.15 mmol, 1.5 equiv) in toluene (0.2 mL) was added catalyst VI (0.005 mmol, 0.05 equiv). The resulting mixture was stirred at room temperature (23C). After the reaction completed, the mixture was quenched with water (5 mL) and extracted with ethyl acetate (2 x 5 mL). The combined organic layer was washed with brine and dried over Na2SO4. The solvent was then removed under reduced pressure. The product was afforded by silica gel flash chromatography using gradient elution (EtOAc/Hexane = 1:10 to 1:6).

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, Ethyl 2-cyano-2-phenylacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tan, Bin; Zhang, Xuan; Zhong, Guofu; ARKIVOC; vol. 2014; 3; (2014); p. 124 – 142;,
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. 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-3-fluorophenylacetonitrile

General procedure: To a 5 mL Schlenk tube were added aryl / heteroaryl acetonitriles 1 (1.0 mmol, 1.0 equiv.), vinyl diphenylsulfonium triflate (434.4 mg, 1.2 mmol, 1.2 equiv.), and DMSO (5 mL). The mixture was stirred at room temperature for 2 min and to the mixture DBU (456 mg, 3 mmol, 3.0 equiv.) was added. The mixture was stirred for 12 hours at room temperature, and then to the mixture was added saturated ammonium chloride solution (25 mL). The resulting mixture was extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with H2O (2 x 30 mL), dried with anhydrous sodium sulfate. After concentration, product 2 was purified using silica gel column chromatography using an appropriate eluent.

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 499983-13-0.

Reference:
Article; Zhou, Mingwei; Hu, Yimin; En, Ke; Tan, Xuefei; Shen, Hong C.; Qian, Xuhong; Tetrahedron Letters; vol. 59; 14; (2018); p. 1443 – 1445;,
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. 145498-86-8, name is Methyl 2-(cyanomethyl)-3-methoxybenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 145498-86-8

Into a 500 mL 3-neck round bottom flask was added 10 g (61.75 mmol) of 2-bromomethyl, 3-methoxy methyl benzoate, 4.0 g (81.6 mmol) of NaCN, 0.30 g (2 mmol) of NaI, 100 mL of CH3CN, and 50 mL of DMF. The reaction mixture was heated and refluxed for 10 hours. The precipitate (NaBr) was filtered off, and the solution was concentrated on an evaporator. 300 mL of water and 200 mL of ether were added and then shaken in a separatory funnel. The water was extracted twice with 100 mL of ether. The ether fractions were dried over MgSO4, and concentrated to yield methyl 3-methoxy-2-cyanomethylbenzoate (95-100% yield). This ester (0.053 mmol, 10.51 g) was stirred vigorously in 100 mL of CH3OH. Ba(OH)2 H2O (0.079 mmol, 14.97 g) was added and the mixture stirred at room temperature overnight. The CH3OH was removed on a rotary evaporator. 150 mL of water, 200 mL of CH2Cl2, and 50 mL of 6N HCl were added, and then stirred in a flask to dissolve all residues. The mixture was transferred to a separatory funnel, acidified with 6N HCl to pH 1-2. The CH2Cl2 phase was separated and the aqueous phase extracted twice with 50 mL of CH2Cl2. The CH2Cl2 extracts were combined, dried over MgSO4 and charcoal, filtered, and evaporated to yield 8.8 g of a white solid, 2-cyanomethyl-3-methoxybenzoic acid, (87%). Methyl 3-methoxy-2-cyanomethylbenzoate: 1H NMR (CDCl3, 300 MHz) delta (ppm): 7.6 (d, 1H), 7.4 (t, 1H), 7.1 (d, 1H), 4.18 (s, 2H), 3.94 (s, 3H), 3.926 (s, 3H). TLC (1:1 ethyl acetate: hexane) 0.55. 2-Cyanomethyl-3-methoxybenzoic acid: 1H NMR (300 Mhz, CDCl3) delta (ppm): 7.55 (d, 1H), 7.45 (t, 1H), 7.3 (d, 1H), 4.121 (d, 2H), 3.91, (s, 3H). TLC (1:1 ethyl acetate: hexane

The synthetic route of 145498-86-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hormann, Robert Eugene; Potter, David W.; Chortyk, Orestes; Tice, Colin M.; Carlson, Glenn Richard; Meyer, Andrew; Opie, Thomas R.; US2006/20146; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts