Category: 101-55-3

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 101-55-3 as follows. HPLC of Formula: C12H9BrO

(1) Grignard reagent: first in a 1000mL three-necked flask, Add 600mLTHF and 200g 4 – Bromodiphenyl ether stirred solution, spare. Then in a 2000mL three-necked flask was added 21.5g of magnesium, 20 mL THF, one small Iodine, 20mL of prepared 4-bromo-diphenyl ether in THF was added dropwise, and after the initiation of heating, the remaining 4-bromo-diphenyl ether in THF was added dropwise at 30-35 C. After the addition, the mixture was incubated at 30-35 C Stirred for 1 hour, The flask was cooled to -30 C with liquid nitrogen until ready for use. (2) Borated: In the above format liquid, 100.1 g of trimethyl borate 600 mL THF solution was slowly added dropwise, Dropping process to maintain -40 ~ -30 the following, After dropping the mixture was allowed to warm to room temperature, 400 ml of 10% hydrochloric acid was added dropwise and refluxed for 1 hour. After distilling off the THF, 500 ml of cold water was added and the mixture was stirred for 30 minutes, cooled, crystallized and separated, 154.1 g of 4-phenoxybenzeneboronic acid were obtained, The yield is 90%. (3) Purification: In a 1 L three-necked flask were added 154.1 g of wet crude 4-phenoxybenzeneboronic acid, Add 200 mL of toluene to dissolve, desolvate, cool, crystallize and centrifuge to obtain 137 g of 4-phenoxybenzeneboronic acid product in a yield of 80%

According to the analysis of related databases, 101-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bengbu Zhong Shi Chemical Co., Ltd.; Yang Qing; Liu Hongqiang; Zhao Shimin; Xu Jianxiao; (5 pag.)CN105820184; (2016); A;,
Ether – Wikipedia,
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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. 101-55-3, name is 1-Bromo-4-phenoxybenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-4-phenoxybenzene

4-bromodiphenyl ether(6.2g, 25.0mmol) Isopropanol pinacol borate (10.3 mL, 50 mmol)Soluble in dry tetrahydrofuran,Cooled to -78C under nitrogen protection.n-Butyllithium (2.5M, 18 mL, 45 mmol) was added dropwise,After completion of the addition, the mixture was stirred for 6 hours and slowly warmed to -40C for 12 hours.The reaction was added to saturated ammonium chloride solution and extracted three times with ethyl acetate.The organic phases were combined and dried over anhydrous sodium sulfate.It was evaporated to dryness by rotary evaporation and purified by column to give 5.4 g of the target compound in a yield of 72%.

The synthetic route of 101-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Chen Deheng; Yan Ziqin; Guo Dexiang; (85 pag.)CN107759602; (2018); A;,
Ether – Wikipedia,
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Electric Literature of 101-55-3, These common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, 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.

The 10.0g (42.8mmol) 4- polybrominated diphenyl ethers dissolved in 100ml of tetrahydrofuran, cooled to -20 , dropping19.2ml (48.0mmol) of n-butyllithium, the reaction was kept 1 hour after dropwise. Then dropping 6.4g (36.0mmol)A compound of formula 3 was dissolved in 30ml of tetrahydrofuran, warmed to 0 deg.] C After the addition, the reaction was continued for 1 hour.Was added dropwise 50ml of saturated ammonium chloride solution, the organic phase was separated. The organic phase was concentrated to give a yellow solid 10.8g,Yield 86.4%.

Statistics shows that 1-Bromo-4-phenoxybenzene is playing an increasingly important role. we look forward to future research findings about 101-55-3.

Reference:
Patent; Okuura Dayton (Shanghai) Pharmaceutical Co., Ltd.; Yu, Libing; Guo, Maojun; Yang, Qingang; Ren, Huasen; (19 pag.)CN105622613; (2016); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 101-55-3, name is 1-Bromo-4-phenoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 101-55-3

4-Bromodiphenyl ether (X = Br) (3.74 g, 15 mmol) was dissolved in 1,4-dioxane (50 ml)Addition of pinacol diboronate(4.52 g, 18 mmol),Potassium acetate (1.78 g, 18 mmol).Then, the catalyst [1,1′-bis (diphenylPhosphine) ferrocene] palladium dichloride [Pd (dppf) 2Cl2] (1.5 mmol, 1.11 g).With stirring, heated to 100 C, the reaction 5h (TLCDetection of raw materials disappear).Then, Intermediate (14) (4.44 g, 10 mmol) was added, and the reaction was maintained at 100 C for 22 hours14 disappears).Then, after distilling off the organic solvent, Intermediate (9) (yellow solid, 3.41 g, yield 70%, chemical purity and optical purity> = 99%) was obtained.

According to the analysis of related databases, 101-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anrun Pharmaceutical (Suzhou) Co., Ltd.; Hong Jian; Liu Guobin; (12 pag.)CN104557945; (2017); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

101-55-3, 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. 101-55-3, name is 1-Bromo-4-phenoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4B. Alternative Preparation of (5) where R 5 is 4-(4-Bromophenoxy)phenyl A solution of 4-bromodiphenyl ether (50 g, 200.7 mmol) in methylene chloride (118 ml) was cooled to 0C and chlorosulfonic acid (14.7 ml, 220.8 mmol) was added dropwise over a 20 minute period. The solution was stirred an additional 10 minutes, warmed to room temperature and stirred an additional 1 hour. To this mixture was added oxalyl chloride (23.6 ml, 270.9 mmol), followed by N,N-dimethylformamide (1.5 ml) as a catalyst, and the mixture refluxed for 2 hours. The mixture was cooled to room temperature, and additional oxalyl chloride (23.6 ml, 270.9 mmol) was added, the mixture refluxed for 3 hours, cooled to room temperature and stirred 12 hours more. The solution was concentrated to an oil, azeotroped several times using methylene chloride and put under high vacuum (1 torr) for several hours until the mixture had completely solidified. This mixture was immediately dissolved in methylene chloride (160 ml) which was added dropwise to a solution of triphenylphosphine (157.0 g, 602 mmol) in methylene chloride (160 ml) containing N,N-dimethylformamide (4 ml, 52.2 mmol). The mixture was stirred 2 hours, diluted with 1M aqueous hydrochloric acid (300 ml) and stirred for 1 hour. The aqueous layer was separated, extracted with methylene chloride (200 ml), and the organic layers were combined, washed with 200 ml of brine, dried (MgSO4) and concentrated in vacuo.The resulting solid was further purified through trituration with 750 ml of hexane. The solid was then dissolved in 750 ml of diethyl ether, extracted with 2M aqueous sodium hydroxide (2 x 350 ml), and the basic aqueous layer back extracted using diethyl ether (2 x 400 ml). The aqueous layer was adjusted to pH 2, extracted with diethyl ether (3 x 200 ml) and the combined organic layers dried (MgSO4) and concentrated to afford 4-(4-bromophenoxy)thiophenol (45.6 g, 81%). 1H-NMR (CDCl3) delta 3.43 (s, 1H), 6.86 (d, J= 8.9 Hz, 2H), 6.89 (d, J= 8.6 Hz, 2H), 7.28 (d, J= 8.6 Hz, 2H), 7.43 (d, J= 8.9 Hz, 2H).

The synthetic route of 1-Bromo-4-phenoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AGOURON PHARMACEUTICALS, INC.; EP780386; (1997); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

101-55-3, Adding some certain compound to certain chemical reactions, such as: 101-55-3, name is 1-Bromo-4-phenoxybenzene, 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 101-55-3.

General procedure: Reactions were conducted using standard dry box techniques and all solvents were distilled over Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.sodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was then purified by column chromatography on silica gel.

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 101-55-3.

Reference:
Article; Semmes, Jeffrey G.; Bevans, Stephanie L.; Mullins, C. Haddon; Shaughnessy, Kevin H.; Tetrahedron Letters; vol. 56; 23; (2015); p. 3447 – 3450;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 101-55-3 name is 1-Bromo-4-phenoxybenzene, 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. 101-55-3

A mixture of compound (III) (Pgi = Pg2 = Boc) (837 mg, 2.00 mmol), PdCl2 (35 mg, 0.20 mmol), 4,4?-di(tert-butyl)-2,2?-bipyridine (54 mg, 0.20 minol), Cs2CO3 (716 mg, 2.20 rnmol), 1-bromo-4-phenoxybenzene (548 mg, 2.20 mmol) and diglyme (10 ml) was heated in a sealed tube under argon atmosphere at 110C for 20 h with intensive stirring. After completion of the reaction the tube was cooled to room temperature, carefully opened, and the reaction mass was poured into EtOAc (40 ml). After intensive stirring for 5 mm the obtained suspension was filtered through celite un evaporated in vacuum. The product was purified by column chromatography (eluent EtOAc-hexane 1:4, Rf 0.3). Yield 727 mg (62%), white amorphous powder.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-phenoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; LEBEDEVS, Antons; PONOMARJOVS, Jurijs; VARACEVA, Larisa; CERNAKS, Dmitrijs; CERNOBROVIJS, Aleksandrs; LAVRINOVICS, Edvards; (15 pag.)WO2017/39425; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, molecular formula is C12H9BrO, 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. 101-55-3.

EXAMPLE 1 1-(2-Methyl-3-butyn-2-ol)-2-(4-phenyloxyphenyl)ethyne Into a 1 L three-necked, round-bottomed flask equipped with a magnetic stirrer, a condenser, and a nitrogen inlet, 4-bromodiphenylether (50.1 g, 201 mmol), freshly distilled 2-methyl-3-butyn-2-ol (64.3 g, 892 mmol), copper(I) iodide (0.11 g, 0.60 mmol), triphenylphosphine (0.33 g, 1.3 mmol), and bis(triphenylphosphine)palladium(II) chloride (1.12 g, 1.6 mmol) were placed. The solids were carefully washed in with triethylamine (500 mL). The mixture was heated under reflux for 24 h. After the reaction mixture had been allowed to cool to room temperature, the solution was filtered through silica gel. The filtrate was poured into 5% hydrochloric acid solution and diluted with methylene chloride. After separation from the aqueous phase, the organic phase was subjected to purification via a silica-gel column chromatography with methylene chloride/hexane elution to give 40.5 g (80% yield) of light yellow oil. Anal. Calcd. for C17H16O2: C, 80.93%; H, 6.39%; O, 12.68%. Found: C, 80.88%; H, 6.43%; O, 12.89%. Mass spectrum (m/e): 252 (M+, 100% relative abundance).

The synthetic route of 1-Bromo-4-phenoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The United States of America as represented by the Secretary of the Air Force; US6979737; (2005); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem