Category: 101-55-3

Synthetic Route of 101-55-3,Some common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, molecular formula is C12H9BrO, 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 (S) -A40.2g (0.64mmol), 4- phenoxy-bromobenzene 0.24g (0.96mmol, 1.5eq.), Palladium acetate 0.013g (0.06mmol, 0.1eq.), BINAP0.037g (0.06mmol after, 0.1eq.), cesium carbonate 0.52g (1.6mmol, 2.5eq.) swap argon, DMF (4mL), the reaction 100 8 h, concentrated after adding saturated brine, extracted with methylene chloride and dried, Biotage silica gel column chromatography (petroleum ether / ethyl acetate = 28%) to give a pale yellow solid A70.27g, yield 87%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-phenoxybenzene, its application will become more common.

Reference:
Patent; Nanjing Yong Shan Biological Technology Co., Ltd.; Wang Yazhou; Jin Qiu; Tang Feng; Huang Wei; Hua Yulin; (10 pag.)CN103113375; (2017); B;,
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Electric Literature of 101-55-3,Some common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, molecular formula is C12H9BrO, 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.

Nanoporous metal gold catalyst (9.8 mg, 0.05 mmol),Ethanol (1.5mL) and 4-bromophenyl phenyl ether(62.27mg, 0.25mmol),Cesium carbonate (364.3 mg, 1.125 mmol) was added to the reaction vessel, and hydrogen (40 bar) was introduced.Heating and stirring, the reaction temperature is controlled at 100 C,The reaction time is controlled at 90h.The reaction solution is extracted with water,Obtained 39.1 mg of biphenyl,The yield was 92%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-phenoxybenzene, its application will become more common.

Reference:
Patent; Dalian University of Technology; Bao Ming; Zhao Yuhui; Feng Xiujuan; Yu Xiaoqiang; Zhang Sheng; (13 pag.)CN109608297; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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., HPLC of Formula: C12H9BrO

[00432] In a reaction tube under nitrogen, a mixture of PdCl2(dppf)CH2Cl2 (22 mg; 0.027 mmol) and triethylamine (0.36 ml; 2.58 mmol) in dioxane (4 ml; dried over 4 ? sieves) was sealed and stirred at 80 C. overnight (18 h). After cooling to room temperature, HB(pin) (0.19 ml;, 1.31 mmol) and 4-bromodiphenyl ether (216 mg; 0.865 mmol) were added and the reaction mixture was stirred at 80 C. GC analysis after 18 h showed a peak at 13.84 mins which was identified by GC/MS as the desired compound.

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

Reference:
Patent; Commonwealth Scientific and Industrial Research Organisation; US6680401; (2004); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products 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.

To a solution of compound 55-1 (16 g, 64 mmol) in TEA (160 mL) was added PPh3 (1.68 g, 6.4 mmol), cuprous iodide (0.6 g, 3.2 mmol), palladium acetate (0.72 g, 3.2 mmol) and trimethylchlorosilane (10.7 g, 96 mmol) and the reaction solution was stirred at 90 C. for 12 h, after which water (100 mL) was added and the resulting solution was extracted with EtOAc (100 mL×4). The organic phases were combined, dried over anhydrous Na2SO4, filtered and evaporated to give a crude product which was purified by column chromatography to afford the title compound 55-2 (yellow solid, 15 g, Yield 88%). 1H NMR (400 MHz, CDCl3): delta ppm 7.45 (d, J=8.78 Hz, 2H), 7.35-7.41 (m, 2H), 7.13-7.19 (m, 1H), 7.04 (d, J=7.78 Hz, 2H), 6.93 (d, J=8.78 Hz, 2H), 0.27 (s, 9H).

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; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 101-55-3, name is 1-Bromo-4-phenoxybenzene, belongs to ethers-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 101-55-3, HPLC of Formula: C12H9BrO

(2) In a 500 ml four-necked flask, 3 g of 4-bromobiphenyl ether and 61 g of diethyl ether and 3.3 g of magnesium wire were put into a 500 ml four-necked flask under the protection of high-purity nitrogen, and Grignard reaction was initiated by rapid stirring at 35 C.,8 ~ 9 hours dropping 4-bromo-diphenyl ether 28g and80g ether solution,40 incubated for 2 hours, cooled to 5 , quickly added mixed coupling agent (cuprous iodide 1.5g, cuprous bromide 1.0g), continue to cool to -16 , temperature -16 ~ 20 ,(15 g of S-epichlorohydrin and 18 g of diethyl ether) was added dropwise for 10 to 11 hours and then incubated at -16 to 20 C for 15 hours, transferred to 65 g of 12% dilute sulfuric acid and stirred at 25 to 30 C for 1 hour,After standing for half an hour, the layers were separated and the ether was distilled and recovered. 120 g of water was added and the mixture was filtered while cooling to 5 C. The wet product was dried at 75 C for 2 hours to obtain (S) -1- (4-diphenylether) -2- Hydroxy-3-chloropropane yield 91.8%, content 95.1%. .

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; Binhai Extensive Chemical Co., Ltd.; Wu Fucai; (8 pag.)CN106957220; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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., category: ethers-buliding-blocks

Example 111 Preparation of 4-phenoxyphenyl-phenylmethanol (127) To a stirred solution of 4-bromodiphenyl ether (2.0 g, 8.03 mmol) in THF (15 mL) at -78 C. was added n-butyllithium (3.85 mL, 2.6 M solution in hexanes). The reaction was stirred under argon for 2 hrs before a solution of benzaldehyde (0.85 g, 8.03 mmol) in THF at -78 C. was added. After stirring at -78 C. for 2 hrs, the reaction was quenched with water and extracted with ether. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the crude product. The crude mixture was purified via flash SiO2 chromatography (ethyl acetate/hexanes (10%/90%) to (15%/85%)) to give 127 (2.22 g, 97% yield): 1H-NMR (400 MHz, chloroform-d) delta 7.28-7.40 (m, 9H), 7.10 (t, J=7.6, 1 H), 6.94-7.01 (m, 4H), 5.84 (d, J=3.6 Hz, 1H), 2.17 (d, J=3.6 Hz, 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; Scanlan, Thomas S.; Hart, Matthew E.; Grandy, David K.; Bunzow, James R.; Miyakawa, Mononori; Tan, Edwin Saavedra; Suchland, Katherine L.; US2005/96485; (2005); A1;,
Ether – Wikipedia,
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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., COA of Formula: C12H9BrO

A mixture of compound (III) (Pgi = Pg2 = Cbz) (973 mg, 2.00 mmol), Pd(OAc)2 (44 mg, 0.20 mmol), 1,10-phenanthroline (36 mg, 0.20 mmol), Cs2CO3 (716 mg, 2.20 mmol), 1-bromo-4- phenoxybenzene (548 mg, 2.20 mmol) and xylene (10 ml) was heated in a sealed tube under argon atmosphere at 140C for 16 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 1:2, Rf 0.4). Yield 995 mg (76%), white amorphous powder.

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

Reference of 101-55-3, 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.

General procedure: Suzuki-coupling reaction was carried out in a 25mL round bottom (RB) flask. Initially, RB was cleaned with water and then rinsed with acetone followed by drying at 60C in an oven for one hour. One mmol of bromobenzene and two mmol of phenylboronic acid were poured into RB. Subsequently, 2mL of toluene was inserted into the RB and closed with a rubber septum. The reaction solution was purged with N2 gas for 30min for the complete removal of air from the mixture. After that, RB was charged with 30mg of Ag/TiO2 photocatalyst, and the vessel was sealed with the rubber septum. The reaction mixture again purged with the N2 gas for the residual air and then irradiated with the 20W white LED (lambda ~ 420nm) for 24h. The sample was analyzed with TLC after every two-hour interval. The conversion and the yield were determined with GC-FID (Thermo equipped with Stabilwax w/Integra- Guard 30-m-long column), and confirmation was obtained by the 1H and 13C NMR of the pure samples.

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; Chen, Yuning; Feng, Li; Journal of Photochemistry and Photobiology B: Biology; vol. 205; (2020);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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., Computed Properties of C12H9BrO

4B. Alternative Preparation of (5) where R5 is 4-(4-Bromophenoxy)phenyl A solution of 4-bromodiphenyl ether (50 g, 200.7 mmol) in methylene chloride (118 mL) was cooled to 0 C. 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*350 mL), and the basic aqueous layer back extracted using diethyl ether (2*400 mL). The aqueous layer was adjusted to pH 2, extracted with diethyl ether (3*200 mL) and the combined organic layers dried (MgSO4) and concentrated to afford 4-(4-bromophenoxy)thiophenol (45.6 g, 81%). 1 H-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 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; Syntex (U.S.A.) Inc.; Agouron Pharmaceuticals, Inc.; US5932595; (1999); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 101-55-3, name is 1-Bromo-4-phenoxybenzene, belongs to ethers-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 101-55-3, SDS of cas: 101-55-3

A THF solution (15 mL) of 1-bromo-4-phenoxybenzene (2.48 g, 10 mmol) was added dropwise to a mixture of Mg (288 mg, 12 mmol) and a small amount of iodine in anhydrous THF (10 mL). After refluxing for 1 h, the Grignard reagent of (4-phenoxyphenyl)magnesium bromide was obtained, which was dissolved in THF and added dropwise to a cooled (-78 C) solution of ethyl pyruvate (1.16 g, 10 mmol). After completion of the addition, the reaction temperature was slowly allowed to rise to 20 C and kept overnight. The reaction mixture was poured into an ice solution of HCl and then extracted with methylene chloride (3 × 40 mL). The methylene chloride extract was washed with brine (30 mL) and dried with MgSO4. Evaporation of methylene chloride at reduced pressure afforded the crude product. After purification by flash column chromatography, the intermediate 7 (1.49 g) was obtained as a pale yellow oil in a yield of 52%. 1H NMR (600 MHz, CDCl3): delta 1.27 (t, J = 7.2 Hz, 1H, CH3), 1.77 (s, 3H, CH3), 3.78 (s, 1H, OH), 4.22-4.27 (m, 2H, CH2), 6.97 (d, J = 9.0 Hz, 2H, ArH), 7.01 (d, J = 7.8 Hz, 2H, ArH), 7.11 (t, J = 7.5 Hz, 1H, ArH), 7.34 (t, J = 7.8 Hz, 2H, ArH), 7.51 (d, J = 8.4 Hz, 2H, ArH).

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, 1-Bromo-4-phenoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Fu; Li, Hui; Wang, Le; Yang, Wen-Chao; Wu, Jia-Wei; Yang, Guang-Fu; Bioorganic and Medicinal Chemistry; vol. 19; 15; (2011); p. 4608 – 4615;,
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