Category: 50638-46-5

Electric Literature of 50638-46-5,Some common heterocyclic compound, 50638-46-5, name is 4-Bromo-3-chloroanisole, molecular formula is C7H6BrClO, 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 1: Preparation of 4-hydroxy-1-(2-chloro-4-methoxyphenyl)-2-methylbutan-1-one [0064] To a 1.0 L, 3-neck round bottom flask, equipped with a mechanical stirrer and an internal thermometer, was added a solution of 4-bromo-3-chloroanisole (12.0 g, 54.0 mmol) in 350 mL of THF under nitrogen. The solution was cooled to -85 C. with a MeOH/liquid nitrogen bath. To this solution was added t-BuLi (72.0 mL, 1.6 M in pentane, 122 mmol) slowly followed by the addition of a solution of alpha-methyl-gamma-butyrolactone (9.25 g, 92.0 mmol) in THF (30.0 mL). The internal temperature was controlled <-80 C. After 1 h stirring at <-80 C., the reaction mixture was quenched with saturated NH4Cl solution and warmed to room temperature. Water and EtOAc were added and separated. The aqueous layer was extracted with EtOAc (2×). The combined organic solutions was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (E:H, 1:3) to give 10.4 g (79%) of brown oil as the title compound: 1H NMR (400 MHz, CDCl3) delta 7.53 (d, J =8.6 Hz, 1H), 6.97 (d, J =2.4 Hz, 1H), 6.85 (dd, J =8.6, 2.4 Hz, 1H), 3.88 (s, 3H), 3.77-3.69 (m, 2H), 3.64-3.56 (m, 1H), 2.16-2.07 (m, 1H), 1.76-1.67 (m, 1H), 1.23 (d, J=7.0 Hz, 3H); MS (El m/z 241.16 (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 4-Bromo-3-chloroanisole, its application will become more common. Reference:
Patent; Pfizer Inc; US2004/204415; (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. 50638-46-5, name is 4-Bromo-3-chloroanisole, A new synthetic method of this compound is introduced below., COA of Formula: C7H6BrClO

Under an argon atmosphere, 1-bromo-2-chloro-4-methoxybenzene (44.3 g) was dissolved in toluene (220 ml), ethyl 2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoate (60.8 g), water (132 ml), sodium hydrogen carbonate (33.6 g) and dichlorobis(triphenylphosphine)palladium(II) (2.8 g) were added, and the mixture was stirred at an oil bath temperature of 120 C. for 7 hr. To the reaction mixture was added ethyl 2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoate (5.2 g), and the mixture was further stirred for 2 hr. The reaction mixture was cooled to room temperature, toluene (100 ml) and water (200 ml) were added, and the mixture was stirred overnight. To the reaction mixture was added activated carbon (3 g), and the mixture was further stirred for 1 hr. The insoluble material was filtered off through celite, and the insoluble material was washed with toluene (100 ml) and water (200 ml). The obtained filtrates were combined to allow for layer separation. The obtained organic layer was washed with water (100 ml), and the solvent was evaporated to give the title compound (67.7 g). [0120] 1H-NMR (400 MHz, DMSO-D6) delta: 7.88-7.86 (1H, m), 7.63 (1H, td, J=7.6, 1.4 Hz), 7.51 (1H, td, J=7.6, 1.4 Hz), 7.27 (1H, dd, J=7.6, 0.9 Hz), 7.18 (1H, d, J=8.6 Hz), 7.06 (1H, d, J=2.6 Hz), 6.95 (1H, dd, J=8.6, 2.6 Hz), 4.01 (2H, m), 3.80 (3H, s), 0.96 (3H, t, J=7.1 Hz)

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; JAPAN TOBACCO INC.; Motomura, Takahisa; Shomi, Gakujun; US2014/296315; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

50638-46-5, name is 4-Bromo-3-chloroanisole, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: chlorides-buliding-blocks

Step 2: (E)-tert-Butyl 3-(4-((E)-2-(2-chloro-4-methoxyphenyl)-2-cyclobutyl-l-(4- morpholinophenyl)vinyl)phen l)acrylate[00401] A mixture of (E)-tert-butyl 3-(4-((Z)-2-cyclobutyl-2-(5,5-dimethyl-l ,3,2-dioxaborinan-2- yl)-l-(4-morpholinophenyl)vinyl)phenyl)acrylate (754 mg, 1.64 mmol), l -bromo-2-chloro-4- methoxybenzene (545 mg, 2.46 mmol), Pd(PPh3)2Cl2(1 15 mg, 0.16 mmol), and KOH (6M, 1.6 mL, 9.9 mmol) in 1 ,4-dioxane (10 mL) was heated to 90C for lh. After cooling, ethyl acetate and brine were added to the reaction mixture and the two layers were separated. The organic layer was washed with more brine, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel to afford 520 mg of the title compound as a yellow foam. 1H NMR (400 MHz, DMSO-d6): delta 7.37-7.33 (m, 3H), 7.1 1 (d, 1H), 7.04 (d, 2H), 6.95-6.90 (m, 5H), 6.82 (m, 1H), 6.34 (d, 1H), 3.74 (m, 4H), 3.71 (s, 3H), 3.42 (m, 1H), 3.13 (m, 4H), 1.87 (m, 3H), 1.67 (m, 2H), 1.46 (m, 1H), 1.43 (s, 9H); LCMS: 586 (M+H)+.

The synthetic route of 50638-46-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SERAGON PHARMACEUTICALS, INC.; SMITH, Nicholas, D.; GOVEK, Steven, P.; KAHRAMAN, Mehmet; BONNEFOUS, Celine; JULIEN, Jackaline, D.; WO2014/151899; (2014); 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. 50638-46-5, name is 4-Bromo-3-chloroanisole, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Bromo-3-chloroanisole

Example 1 Preparation of diethyl 2-chloro-4-methoxyphenylmalonate At about 60 C., diethyl malonate (0.49 mol) was added, over a period of 2 hours, to a suspension of sodium hydride (0.51 mol) in 140 ml of 1,4-dioxane. After a further 10 min of stirring, 0.05 mol of CuBr was added. After 15 min, 0.25 mol of 1-bromo-2-chloro-4-methoxybenzene in 10 ml of dioxane was added. The reaction mixture was kept at 100 C. for about 14 hours, and 35 ml of 12N hydrochloric acid were then added slowly at about 15 C. The precipitate was filtered off and the filtrate was extracted with diethyl ether. After phase separation, the organic phase was dried and then freed from the solvent. 34 g of the title compound remained.

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; Tormo i Blasco, Jordi; Biettner, Carsten; Muller, Bernd; Gewehr, Markus; Grammenos, Wassilios; Grote, Thomas; Rheinheimer, Joachim; Schafer, Peter; Schieweck, Frank; Schwogler, Anja; Wagner, Oliver; Scherer, Maria; Strathmann, Siegfried; Schofl, Ulrich; Stierl, Reinhard; US2007/149400; (2007); 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. 50638-46-5, name is 4-Bromo-3-chloroanisole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Bromo-3-chloroanisole

A mixture of 1 -bromo-2-chloro-4-methoxybenzene (1.5 g, 6.8 mmol), oxazole (878 mg, 12.7 mmol), /-BuOK (1.52 g, 13.5 mmol) and tetrakis (1.56 g, 1.35 mmol) in dioxane (10 mL) was heated to 100C under N2 atmosphere for 4 hr. After cooling to r.t., the reaction mixture was concentrated under reduced pressure to give the crude product which was purified by flash chromatography (silica gel, 0 to 25% EA in PE) to afford 2-(2-chloro-4-methoxyphenyl)oxazole (40) (600 mg, 42 % yield) as a yellow solid. LC-MS (ESI): mlz (M+l) 210.0.

According to the analysis of related databases, 50638-46-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACYCLICS LLC; CHEN, Wei; WANG, Longcheng; YAN, Shunqi; LOURY, David, J.; JIA, Zhaozhong, J.; FRYE, Leah, Lynn; GREENWOOD, Jeremy, Robert; SHELLEY, Mee, Yoo; ATALLAH, Gordana, Babic; ZANALETTI, Riccardo; CATALANI, Maria, Pia; RAVEGLIA, Luca, Francesco; (402 pag.)WO2016/4272; (2016); 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. 50638-46-5, name is 4-Bromo-3-chloroanisole, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-3-chloroanisole

A 1.6M solution of n-butyllithium in hexane (4 ml) was added to a solution of 4-bromo-3-chloroanisole (CAS Reg. No. 50638-46-5, 1.3 g) in THF (20 ml) at -78 C. The mixture was stirred for 30 min at -78 C. Acetaldehyde (0.7 ml) was added to the mixture. The mixture was allowed to warm to room temperature. Water (50 ml) was added and extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated to an oil to give the title compound (983 mg) as colorless oil. MS (m/e)=186 [M+].

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; Hunziker, Daniel; Lerner, Christian; Mueller, Werner; Sander, Ulrike Obst; Pflieger, Philippe; Waldmeier, Pius; US2010/249124; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 50638-46-5, The chemical industry reduces the impact on the environment during synthesis 50638-46-5, name is 4-Bromo-3-chloroanisole, I believe this compound will play a more active role in future production and life.

Step C: Preparation of a-(2-chloro-4-methoxyphenyl)- 1 -(2,6-difluorophenyl)- 1H- imidazole-5 -methanol; To a mixture of l-bromo-2-chloro-4-methoxybenzene (5.31 g, 24.0 mmol) in tetrahydrofuran (40 mL) cooled in an ice-water bath was added dropwise isopropylmagnesium chloride lithium chloride complex (1.3 M tetrahydrofuran, 18.4 mL, 24.0 mmol) over 15 minutes. The reaction mixture was allowed to warm to ambient temperature (about 20 C) and stirred for 16 h. After 16 h, the reaction mixture was cooled to 0 C and l-(2,6-difluorophenyl)-lH-imidazole-5-carboxaldehyde (i.e. the product of Step B) (2.50 g, 12.0 mmol) in tetrahydrofuran (10 mL) was added dropwise. The reaction mixture was stirred for about 15 minutes, and then saturated aqueous ammonium chloride solution (about 3 mL) was added. After about 5 minutes more saturated aqueous ammonium chloride solution (about 100 mL) was added and the resulting mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound as a white solid (2.77 g).in NMR (CDCI3): delta 7.51 (s, 1H), 7.43 (m, 1H), 7.38 (d, 1H) 7.1-7.0 (m, 2H), 6.9 (m, 1H), 6.82 (m, 1H), 6.78 (m, 1H), 5.98 (m, 1H), 3.80 (s, 3H), 2.4 (m, 1H).

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, 4-Bromo-3-chloroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; LONG, Jeffrey, Keith; BEREZNAK, James, Francis; KAR, Moumita; TAGGI, Andrew, Edmund; CHEN, Yuzhong; WO2012/44650; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 50638-46-5, name is 4-Bromo-3-chloroanisole, 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 50638-46-5, HPLC of Formula: C7H6BrClO

Step 1 Ethyl 2?-chloro-4?-methoxybiphenyl-2-carboxylate [0117] 1-bromo-2-chloro-4-methoxybenzene (44.3 g) was dissolved in toluene (220 ml), ethyl 2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoate (60.8 g), water (132 ml), sodium hydrogen carbonate (33.6 g) and dichlorobis(triphenylphosphine)palladium(II) (2.8 g) were added, and the mixture was stirred at an oil bath temperature of 120 C. for 7 hr. To the reaction mixture was added ethyl 2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoate (5.2 g), and the mixture was further stirred for 2 hr. The reaction mixture was cooled to room temperature, toluene (100 ml) and water (200 ml) were added, and the mixture was stirred overnight. To the reaction mixture was added activated carbon (3 g), and the mixture was further stirred for 1 hr. The insoluble material was filtered off through celite, and the insoluble material was washed with toluene (100 ml) and water (200 ml). The obtained filtrates were combined to allow for layer separation. The obtained organic layer was washed with water (100 ml), and the solvent was evaporated to give the title compound (67.7 g). [0119] 1H-NMR (400 MHz, DMSO-D6) delta: 7.88-7.86 (1H, m), 7.63 (1H, td, J=7.6, 1.4 Hz), 7.51 (1H, td, J=7.6, 1.4 Hz), 7.27 (1H, dd, J=7.6, 0.9 Hz), 7.18 (1H, d, J=8.6 Hz), 7.06 (1H, d, J=2.6 Hz), 6.95 (1H, dd, J=8.6, 2.6 Hz), 4.01 (2H, m), 3.80 (3H, s), 0.96 (3H, t, J=7.1 Hz).

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, 4-Bromo-3-chloroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MOTOMURA, Takahisa; MATSUO, Takuya; SHOMI, Gakujun; INOUE, Masafumi; US2015/25120; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 50638-46-5, These common heterocyclic compound, 50638-46-5, name is 4-Bromo-3-chloroanisole, 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-bromo-2-chloro-4-methoxybenzene (6.6 g, 30 mmoL) in 1, 4-dioxane (150 mL) was added with 4, 4, 5, 5-tetramethyl-2- (1, 4-dioxaspiro [4.5] dec-7-en-8-yl) -1, 3, 2-dioxaborolane (8 g, 30 mmol) , Pd (dppf)2Cl2(2.2 g, 3 mmol) and Cs2CO3(14.7 g, 45 mmol) and the mixture was heated at 90 overnight. After evaporated the solvent under reduced pressure, the residue was added with water (80 mL) , extracted with ethyl acetate (80 mL) . The organic layer was dried, concentrated and purified by column chromatography (PE: EA=80: 1) to give product as a white solid (6.2 g in 74%yield) .1H NMR (CDCl3) deltaH7.12 (d, J = 12.0 Hz, 1H) , 6.90 (d, J = 1.2 Hz, 1H) , 6.75 (dd, J1=8.0 Hz, J2=4.0 Hz, 1H) , 5.56-5.54 (m, 1H) , 4.04-4.01 (m, 4H) , 3.79 (s, 3H) , 2.55-2.51 (m, 2H) , 2.45-2.42 (m, 2H) , 1.89 (t, J = 6.4 Hz, 2H) . [M+H]+=281.1.

Statistics shows that 4-Bromo-3-chloroanisole is playing an increasingly important role. we look forward to future research findings about 50638-46-5.

Reference:
Patent; BEIGENE, LTD.; WANG, Hexiang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHANG, Guoliang; ZHOU, Changyou; (353 pag.)WO2018/54365; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 50638-46-5, name is 4-Bromo-3-chloroanisole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-Bromo-3-chloroanisole

A solution of PdCl2(dppf)-DCM adduct (0.922 g, 1.129 mmol), methylboronic acid (2.70 g, 45.2 mmol), 4-bromo-3-chloroanisole (6.39 ml, 45.2 mmol), and potassium phosphate (28.8 g, 135 mmol) in 150 mL dioxane and 50 mL water was heated to 110 C. for 2 hours. The reaction mixture was then diluted with heptane, the organics dried over MgSO4 and concentrated to afford 2-chloro-4-methoxy-1-methylbenzene. m/z (ESI) 141.0 (M-CH3)+.

The synthetic route of 50638-46-5 has been constantly updated, and we look forward to future research findings.

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