Category: 54788-38-4

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. 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Chloro-4-methoxy-1-methylbenzene

The residue from the previous step was dissolved in 100 mL dioxane, was treated with bis(pinacolato)diboron (11.47 g, 45.2 mmol), potassium phosphate (28.8 g, 135 mmol), XPhos (0.215 g, 0.452 mmol) and (Xphos) palladium(II) phenethylamine chloride (0.334 g, 0.452 mmol) and was heated to 100 C. After stirring overnight, the reaction mixture was concentrated. Silica gel column chromatography (0-20% EtOAc/heptane) gave 2-(5-methoxy-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.80 g, 31.4 mmol, 69.6% yield over two steps). m/z (ESI) 249.3 (M+H)+.

According to the analysis of related databases, 54788-38-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 54788-38-4, These common heterocyclic compound, 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, 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.

Referecne Example 1; (3-Bromophenyl) (4-chloro-2-hydroxy-5-methylphenyl) methanone; Aluminum chloride (20.4 g) was added to a solution of 3-chloro-4-methylanisole (20 g) in chlorobenzene (56 ml) at 20-30C, and then 3-bromobenzoyl chloride (28 g) was further added dropwise over about 30 minutes at 25 to 30C. After completion of addition, the mixture was stirred at 25C for 1 hour, and then heated at 40C for 1 hour. After the reaction was completed, the mixture was cooled, and toluene/tetrahydrofuran (1: 1,200 ml) was added dropwise at 20 to 30C. Then, 4N hydrochloric acid (80 ml) was added dropwise. The organic layer was separated, washed successively with 2N hydrochloric acid (60 ml) and a 10% aqueous sodium chloride solution. The organic layer was concentrated to 80 g. After methanol (100 ml) was added, the mixture was concentrated again to 90 g. Methanol (80 ml) was added to the residue, the mixture was stirred at room temperature for 30 minutes, and below 5C for 1 hour. Crysatls were collected, washed with cooled methanol (40 ml) and dried under reduced pressure to obtain the title compound (35.4 g, yield 85.1 %). H-NMR (300MHz, CDC13) 5 (ppm): 2.28 (3H, s), 7.12 (1H, s), 7.36-7. 42 (2H, m), 7.54-7. 57 (1H, m), 7.72-7. 80 (2H, m), 11.7 (1H, s).

The synthetic route of 54788-38-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/82879; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, belongs to chlorides-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 54788-38-4, HPLC of Formula: C8H9ClO

To 2-chloro-4-methoxytoluene (344 muL, 2.5 mmol, 1.0 eq.) in MeCN (1.5 mL) at 0C is added NBS (500 mg, 3.0 mmol, 1.2 eq.) in 2 portions (2nd half after 30 min stirring). The reaction mixture is allowed to stir at r.t. for 18h. The solvent is removed in vacuo, and the residue is dissolved in DCM and washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the expected product as a mixture, which is used as such in the next step

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; GALAPAGOS NV; LES LABORATOIRES SERVIER; LABEGUERE, Frederic, Gilbert; HENG, Rama; DE CEUNINCK, Frederic, Andre; ALVEY, Luke, Jonathan; AMANTINI, David; BREBION, Franck, Laurent; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene; PEIXOTO, Christophe; POP-BOTEZ, Iuliana, Ecaterina; VARIN, Marie, Laurence, Claire; (180 pag.)WO2017/211666; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, A new synthetic method of this compound is introduced below., Formula: C8H9ClO

Acetic anhydride (10 mL) at-10 oC was treated with concentrated nitric acid (>69% pure, 1 mL) and then treated portionwise with 2-CHLORO-4-METHOXY-1-METHYLBENZENE (0. 78G, 5 mmol) at a rate that maintained the internal temperature lower THAN-5 C. The solution was stirred for additional one hour while warming to room temperature, poured into an ice and water mixture, and extracted with ethyl acetate several times. The organic layers were combined, washed with 10% NA2C03 and brine, dried (MGS04), and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel eluting with 9: 1 hexanes/ethyl acetate to provide 0.75g (71%) of the desired product. MS (DCI) m/e 219 (M+NH4) + ; IH NMR (CDC13, 300 MHz) 8 7.78 (s, 1H), 7.09 (s, 1H), 3.94 (s, 3H), 2.35 (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; ABBOTT LABORATORIES; WO2004/76424; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 54788-38-4

General procedure: To anhydrous THF (6.4 mL) in a dry round-bottom flask was added nickel(II)bromide (279 mg, 1.28 mmol), zinc powder (250 mg, 3.83 mmol), and triphenylphosphine (1.68 g, 6.39 mmol). The mixture was heated to 50 C and stirred for 30 min. The selected o-chlorotoluene (8a or 8b, 12.78 mmol) was added, the temperature raised to 60 C, and the reaction was tightly capped and allowed to stir 30 min, then potassium cyanide (1.66 g, 25.5 mmol) was added over the course of 5 h in 2 equal portions. The mixture was allowed to stir an additional 16 h. Water was added to quench the reaction, and the suspension extracted 3× with ether. The resulting organic layer was washed with H2O and brine, dried over MgSO4, filtered, and concentrated to a heterogeneous mixture of white crystals and clear oil. The residue was diluted with 10 mL of toluene, then methyl iodide (997 mg, 7.02 mmol) was added and allowed to stir 16 h at room temperature. The resulting white crystals were removed via vacuum filtration. The filtrate was concentrated in vacuo to a clear oil. Flash chromatography with 2% EtOAc/hex delivered the pure product in 68-90% yield.

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:
Article; Yestrepsky, Bryan D.; Xu, Yuanxi; Breen, Meghan E.; Li, Xiaoqin; Rajeswaran, Walajapet G.; Ryu, Jenny G.; Sorenson, Roderick J.; Tsume, Yasuhiro; Wilson, Michael W.; Zhang, Wenpeng; Sun, Duxin; Sun, Hongmin; Larsen, Scott D.; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1880 – 1897;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H9ClO

The residue from the previous step was dissolved in 100 mL dioxane, was treated with bis(pinacolato)diboron (11.47 g, 45.2 mmol), potassium phosphate (28.8 g, 135 mmol), XPhos (0.215 g, 0.452 mmol) and (Xphos) palladium(II) phenethylamine chloride (0.334 g, 0.452 mmol) and was heated to 100 C. After stirring overnight, the reaction mixture was concentrated. Silica gel column chromatography (0-20% EtOAc/heptane) gave 2-(5-methoxy-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.80 g, 31.4 mmol, 69.6% yield over two steps). m/z (ESI) 249.3 (M+H)+.

According to the analysis of related databases, 54788-38-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 54788-38-4, These common heterocyclic compound, 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, 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.

Referecne Example 1; (3-Bromophenyl) (4-chloro-2-hydroxy-5-methylphenyl) methanone; Aluminum chloride (20.4 g) was added to a solution of 3-chloro-4-methylanisole (20 g) in chlorobenzene (56 ml) at 20-30C, and then 3-bromobenzoyl chloride (28 g) was further added dropwise over about 30 minutes at 25 to 30C. After completion of addition, the mixture was stirred at 25C for 1 hour, and then heated at 40C for 1 hour. After the reaction was completed, the mixture was cooled, and toluene/tetrahydrofuran (1: 1,200 ml) was added dropwise at 20 to 30C. Then, 4N hydrochloric acid (80 ml) was added dropwise. The organic layer was separated, washed successively with 2N hydrochloric acid (60 ml) and a 10% aqueous sodium chloride solution. The organic layer was concentrated to 80 g. After methanol (100 ml) was added, the mixture was concentrated again to 90 g. Methanol (80 ml) was added to the residue, the mixture was stirred at room temperature for 30 minutes, and below 5C for 1 hour. Crysatls were collected, washed with cooled methanol (40 ml) and dried under reduced pressure to obtain the title compound (35.4 g, yield 85.1 %). H-NMR (300MHz, CDC13) 5 (ppm): 2.28 (3H, s), 7.12 (1H, s), 7.36-7. 42 (2H, m), 7.54-7. 57 (1H, m), 7.72-7. 80 (2H, m), 11.7 (1H, s).

The synthetic route of 54788-38-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/82879; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., 54788-38-4

(a) Synthesis of (3-bromophenyl)(4-chloro-2-hydroxy-5-methylphenyl)methanone aluminium chloride (102 g) was added to a solution of 3-chloro-4-methylanisole (97 g) in chlorobenzene (300 ml) under ice-cooling, and 3-bromobenzoyl chloride (136 g) was further added dropwise over 1 hour.. After completion of addition, the mixture was stirred at room temperature for 30 minutes, and further heated at 120C for 30 minutes.. The reaction solution was ice-cooled, ethyl acetate (600 ml), methanol (100 ml) and 4N hydrochloric acid (400 ml) were added successively, and the mixture was stirred at room temperature for 30 minutes.. The organic layer was washed successively with 1N hydrochloric acid and an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and a solvent was distilled off under reduced pressure.. The residue was purified by recrystallizing from ethyl acetate-hexane, to obtain the title compound (186 g, yield 89%). mp: 115-127C.

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; Takeda Chemical Industries, Ltd.; EP1471064; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, molecular formula is C8H9ClO, 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. 54788-38-4

Intermediate 49a: 1-Bromomethyl-2-chloro-4-methoxy-benzene BR A suspension of 3-chloro-4-methylanisole (2.23 g, 14. 24 mmol), N-bromosuccinimide (2.53 g, 14.24 MMOL), and 70% benzoyl peroxide (493 mg, 1.424 MMOL) in 40 mL CCI4 was heated to reflux at 80C for two hours. The mixture was cooled to room temperature, filtered, and the filtrate was concentrated under rotary evaporator. The residue was purified by flash column chromatography eluting with 5% EtOAc in Hexane to provide 2.25 g of intermediate 49a as a white SOLID. 1H NMR (300 MHz, CDCl3) 8 7.33 (d, 1H, J = 8.48 HZ), 6.93 (d, 1H, J = 2.63 Hz), 6.81-6. 75 (m, 1 H), 4.58 (m, 2H), 3.79 (m, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-methoxy-1-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; WO2005/21554; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics