Category: 57381-49-4

Some common heterocyclic compound, 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, molecular formula is C7H3BrClN, 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: 57381-49-4

To a solution of 2-bromo-4-chlorobenzonitrile (500 mg, 2.3 mmol), in dry THF (50 mL) was added slowly borane-THF complex (1 M, 12 mL, 1 1 .5 mmol) at 0 C before refluxing for 1 h. After cooling down, 1 M HCI in MeOH (20 mL) was charged slowly with ice cooling. The solvent was removed by concentration in vacuo before water (0.61 mmol/mL to benzonitrile) was charged, then washed by Et20 (0.61 mmol/mL to benzonitrile) before basifying with 2 M NaOH solution to pH 12. Et20 (15 mL) was added and the mixture was washed with water (3 x 15 mL) and brine (1 mL). The organic phase was dried (MgS04) and concentrated in vacuo to give a yellow oil (345 mg, 68%). LCMS (EST) m/z = 220.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57381-49-4, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; CHESSARI, Gianni; HOWARD, Steven; BUCK, Ildiko Maria; CONS, Benjamin David; JOHNSON, Christopher Norbert; HOLVEY, Rhian Sara; REES, David Charles; ST. DENIS, Jeffrey David; TAMANINI, Emiliano; GOLDING, Bernard Thomas; HARDCASTLE, Ian Robert; CANO, Celine Florence; MILLER, Duncan Charles; CULLY, Sarah; NOBLE, Martin Edward Maentylae; OSBORNE, James Daniel; PEACH, Joanne; LEWIS, Arwel; HIRST, Kim Louise; WHITTAKER, Benjamin Paul; WATSON, David Wyn; MITCHELL, Dale Robert; (293 pag.)WO2017/55860; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, 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. HPLC of Formula: C7H3BrClN

A flask which had been dried by heating and flushed with argon was initially charged with 1.0 eq. of the appropriate boronic acids, 1.0 eq. of the aryl bromide or aryl iodide, 3.0 eq. of potassium carbonate and 0.1 eq. of [1,1 -bis(diphenylphosphino)ferrocenelpalladium(II) chloride/monodichloromethane adduct or tetrakis(triphenylphosphine)palladium(0). The flask was then evacuated three times and in each case vented with argon. Dioxane (about 6 ml/mmol) was added, and the reaction mixture was stirred at 110 C. for a number of hours until substantially complete conversion had been achieved. The reaction mixture was then filtered through Celite and the filtrate was concentrated under reduced pressure. Water was added to the residue. After addition of ethyl acetate and phase separation, the organic phase was washed once with water and once with saturated aqueous sodium chloride solution, dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure. The crude product was then purified either by means of normal phase chromatography (cyclohexane/ethyl acetate mixtures or dichloromethane/methanol mixtures) or preparative RP-HPLC (water/acetonitrile gradient or water/methanol gradient).

The synthetic route of 2-Bromo-4-chlorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; US2018/346424; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, 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 57381-49-4, Quality Control of 2-Bromo-4-chlorobenzonitrile

Borane tetrahydrofuran complex (55 mL, 1.0 M in THF) were provided with ice cooling, then slowly a solution of 2-bromo-4-chlorobenzonitrile (4.00 g, 18.5 mmol) in THF (10 mL) was added. Thereafter the reaction-mixture was heated under reflux for 16 hours. The reaction was quenched by addition of methanol. 20 mL of hydrochloric acid (1.0 N) were added dropwise with ice cooling. The solution was rendered alkaline with 1.0 M sodium hydroxide solution and extracted with dichloromethane. The organic phase was dried over sodium sulfate and evaporated to yield 2.10 g (36%) of the title compound as the off-white solid. The reaction was monitored by TLC (ethyl acetate/petroleum ether=1 :1, Rf = 0.3). MS (ESIpos): m/z = 220 [M+H]+.

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; BAYER PHARMA AKTIENGESELLSCHAFT; WORTMANN, Lars; SAUTIER, Brice; EIS, Knut; BRIEM, Hans; BOeHNKE, Niels; VON NUSSBAUM, Franz; HILLIG, Roman; BADER, Benjamin; SCHROeDER, Jens; PETERSEN, Kirstin; LIENAU, Philip; WENGNER, Antje, Margret; MOOSMAYER, Dieter; WANG, Qiuwen; SCHICK, Hans; (510 pag.)WO2018/172250; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 57381-49-4, 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 57381-49-4 as follows.

Into a 19-mL sealed tube was placed 2-bromo-4-chlorobenzonitrile (216 mg, 1.00 mmol), dioxane (1.5 mL), water (0.3 mL), Pd(dppf)Cl2 (36 mg, 0.05 mmol), Na2CO3 (318 mg, 2.97 mmol), and phenylboronic acid (148 mg, 1.21 mmol). The resulting solution was stirred for 16 h at 95oC. The reaction was then quenched by the addition of 25 mL of water. The resulting solution was extracted with ethyl acetate (3×15 mL) and the organic layers were combined. The organic layer was washed with brine (25 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue purified via a silica gel chromatography with ethyl acetate/petroleum ether (1:20). This resulted in 50 mg (23% yield) of 4-chloro-2-phenylbenzonitrile as a white solid.1H NMR (400 MHz, DMSO-d6, ppm): delta 8.00 (d, J = 8.4 Hz, 1H), 7.74 (d, J = 2.1 Hz, 1H), 7.68 (dd, J = 8.3, 2.2 Hz, 1H), 7.65 – 7.59 (m, 2H), 7.58- 7.48 (m, 3H), 4.04 (dd, J = 1.9, 1.0 Hz,1H).

According to the analysis of related databases, 57381-49-4, the application of this compound in the production field has become more and more popular.

Reference of 57381-49-4,Some common heterocyclic compound, 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, molecular formula is C7H3BrClN, 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 solution of 2-bromo-4-chlorobenzonitrile (20.0 g, 138.6 mmol) in anhydrous THF (200 mL) at 0 C was added borane (277 mL, 277.2 mmol, 1.0 M) in THF dropwise undera nitrogen atmosphere. The resulting mixture was stirred at 22 C for 1 h and refluxed for 3 h. The reaction was quenched with 2N HC1 (300 mL) at 0 C and then stirred at 70C for 1 h. After cooling to room temperature, the solution was extracted with DCM (400 mL) and the aqueous phase was adjusted to pH = 8 by using 2N NaOH. The mixture was extracted with DCM (300 mL x 3). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo to givethe title compound (12 g, 59%) as yellow oil. ?HNMR (400 IVIFIz, CDC13) 7.55 -7.53 (m, 1H),7.34 – 7.29 (m, 1H), 7.28 – 7.23 (m, 1H), 3.86 (s, 2H).

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-chlorobenzonitrile, its application will become more common.

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. 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Bromo-4-chlorobenzonitrile

Example 6A2-Bromo-4-chlorobenzylamine; 13.9 ml (13.9 mmol) of borane-THF complex (1 M) are provided with ice cooling. Slowly a solution of 604 mg (2.8 mmol) of 2-bromo-4-chlorobenzonitrile (Example 1A) in 60 ml of THF is added. Thereafter the reaction mixture is heated under reflux for 1 h, cooled, and 20 ml of 1N hydrochloric acid are added dropwise with ice cooling. For the work up, the solution is rendered alkaline with a 1N sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried over sodium sulfate and concentrated on a rotary evaporator. The crude product (450 mg, about 73% pure) is reacted further without purification.1H NMR (300 MHz, CDCl3): delta=3.89 (s, 2H), 7.35-7.45 (m [ABM], 2H), 7.55 (d, 1H).

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 57381-49-4.

Some common heterocyclic compound, 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, molecular formula is C7H3BrClN, 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. HPLC of Formula: C7H3BrClN

To a solution of 2-bromo-4-chlorobenzonitrile (500 mg, 2.3 mmol), in dry THF (50 mL) was added slowly borane-THF complex (1 M, 12 mL, 1 1 .5 mmol) at 0 C before refluxing for 1 h. After cooling down, 1 M HCI in MeOH (20 mL) was charged slowly with ice cooling. The solvent was removed by concentration in vacuo before water (0.61 mmol/mL to benzonitrile) was charged, then washed by Et20 (0.61 mmol/mL to benzonitrile) before basifying with 2 M NaOH solution to pH 12. Et20 (15 mL) was added and the mixture was washed with water (3 x 15 mL) and brine (1 mL). The organic phase was dried (MgS04) and concentrated in vacuo to give a yellow oil (345 mg, 68%). LCMS (EST) m/z = 220.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57381-49-4, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; CHESSARI, Gianni; HOWARD, Steven; BUCK, Ildiko Maria; CONS, Benjamin David; JOHNSON, Christopher Norbert; HOLVEY, Rhian Sara; REES, David Charles; ST. DENIS, Jeffrey David; TAMANINI, Emiliano; GOLDING, Bernard Thomas; HARDCASTLE, Ian Robert; CANO, Celine Florence; MILLER, Duncan Charles; CULLY, Sarah; NOBLE, Martin Edward Maentylae; OSBORNE, James Daniel; PEACH, Joanne; LEWIS, Arwel; HIRST, Kim Louise; WHITTAKER, Benjamin Paul; WATSON, David Wyn; MITCHELL, Dale Robert; (293 pag.)WO2017/55860; (2017); 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. 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

Step 1 4-chloro-2-(2,5-dimethoxypyridin-4-yl)benzonitrile 185b 2-Bromo-4-chloro-benzonitrile 185a (5.92 g, 27.33 mmol, prepared by a known method disclosed in “”) was dissolved in 180 mL 1,4-dioxane, then compound 1d (5 g, 27.33 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (2.03 g, 2.73 mmol) and potassium carbonate (11.33 g, 81.98 mmol) were added. Under an argon atmosphere, the reaction solution was warmed up to 110C, and stirred for 16 hours. The reaction solution was naturally cooled to room temperature, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column with elution system B to obtain the title compound 185b (6.5 g, yield: 86.59%).

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 57381-49-4.

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; YANG, Fanglong; WANG, Weimin; LI, Xiaodong; CHEN, Gang; HE, Feng; TAO, Weikang; (198 pag.)EP3486242; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 57381-49-4, A common heterocyclic compound, 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, molecular formula is C7H3BrClN, 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.

[1,1′-bis(diphenylphosphino)dicene. Iron] Palladium dichloride (192.8 mg, 0.26 mmol) and potassium carbonate (1.09 g,7.91mmol) wereadded. The reaction mixture was heated to 110C and the reaction was stirred for 16 hours.The reaction solution was allowed to cool to room temperature and20 mL of water was addedto the reaction mixture. The mixture was extracted with ethyl acetate (20 mL ¡Á 3). The organic phases were combined and the organic phase was washed with saturated sodium chloride solution (20 mL ¡Á2) and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure.The resulting residue was purifiedby silica gel column chromatography using an eluent system C togive the crude title product 4d (450 mg, yellow viscous product), which was directly introduced into the next reaction.

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; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; Yang Fanglong; Chi Jiangtao; He Feng; Tao Weikang; (33 pag.)CN107793396; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 57381-49-4, 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. 57381-49-4 name is 2-Bromo-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.

General procedure: General Method 2A: Suzuki Coupling A flask which had been dried by heating and flushed with argon was initially charged with 1.0 eq. of the appropriate boronic acids, 1.0 eq. of the aryl bromide or aryl iodide, 3.0 eq. of potassium carbonate and 0.1 eq. of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/monodichloromethane adduct or tetrakis(triphenylphosphine)palladium(0). The flask was then evacuated three times and in each case vented with argon. Dioxane (about 6 ml/mmol) was added, and the reaction mixture was stirred at 110 C. for a number of hours until substantially complete conversion had been achieved. The reaction mixture was then filtered through Celite and the filtrate was concentrated under reduced pressure. Water was added to the residue. After addition of ethyl acetate and phase separation, the organic phase was washed once with water and once with saturated aqueous sodium chloride solution, dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure. The crude product was then purified either by means of normal phase chromatography (eluent: cyclohexane/ethyl acetate mixtures or dichloromethane/methanol mixtures) or preparative RP-HPLC (water/acetonitrile gradient or water/methanol gradient). Example 2.1B 4-Chloro-2-(2,5-dimethoxypyridin-4-yl)benzonitrile According to General Method 2A, 7.87 g (95% purity, 40.86 mmol) of 2,5-dimethoxypyridin-4-ylboronic acid were reacted with 8.85 g (40.86 mmol) of 2-bromo-4-chlorobenzonitrile in the presence of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/dichloromethane monoadduct. Yield: 6.23 g (92% purity, 51% of theory). LC/MS [Method 1]: Rt=1.08 min; MS (ESIpos): m/z=275 (M+H)+.

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; HILLISCH, Alexander; STRAssBURGER, Julia; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; BUCHMUeLLER, Anja; GERDES, Christoph; SCHAeFER, Martina; TELLER, Henrik; JIMENEZ NUNEZ, Eloisa; SCHIROK, Hartmut; KLAR, Juergen; LOBELL, Mario; (39 pag.)US2017/283412; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts