Category: 588-96-5

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. 588-96-5, name is p-Bromophenetole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 588-96-5

Ethyl 1-(4-ethoxyphenyl)-1H-pyrazole-3-carboxylate (2) A 10 mL Schlenk tube was dried under vacuum, filled with nitrogen and consecutively charged with 19.4 mg (0.102 mmol, 0.2 eq) Cul, 332.3 mg (1.020 mmol, 2.0 eq) Cs2CO3, 100.0 mg (0.714 mmol, 1.4 eq) ethyl 1H-pyrazole-3-carboxylate (6), 102.4 mg (73.0 muL, 0.510 mmol, 1.0 eq) p-bromophenetol and 1 mL dry ACN. The light brown suspension was degassed by vaccum/N2 cycles and stirred first at 82 C. for 7 h and than after adding 0.5 mL dry DMF (solubility issue) at 120 C. for further 65 h. The GC-MS analysis showed full conversion. ACN and DMF were removed under high pressure and the brown residue was suspended in 10 mL EtOAc. After filtration of the brown suspension through a pad of silica and flushing with 150 mL EtOAc the colorless filtrate was concentrated under reduced pressure leading to 52.1 mg (39%) crude product as a green-brown oil. Final purification by column chromatography (CH/EtOAc 3:1, size: 15.5*2.0 cm, 20 g silica gel) yielded the pure title compound. yield: 10.2 mg (8%); orange solid; M.p.: 88-90 C.; Rf (CH/EtOAc 3:1): 0.40; 1H-NMR (300 MHz, DMSO-d6): delta (ppm)=8.51 (d, 4J=2.4 Hz, 1H, Ar-H), 7.78 (d, 3J=9.0 Hz, 2H, Ar-H), 7.07 (d, 3J=9.0 Hz, 2H, Ar-H), 6.97 (d, 4J=2.4 Hz, 1H, Ar-H), 4.31 (q, 3J=6.9 Hz, 2H, CH2), 4.08 (q, 3J=7.2 Hz, 2H, CH2), 1.37-1.29 (m, 6H, 2 CH3); 13C-NMR (75.5 MHz, DMSO-d6): delta (ppm)=161.4 (C=O), 157.6 (Cq), 143.6 (Cq), 132.5 (Cq), 129.5 (CHAr), 120.7 (2CHAr), 115.0 (2CHAr), 119.8 (CHAr), 63.4 (CH2), 60.3 (CH2), 14.5 (CH3), 14.1 (CH3); GC-MS (NM-50_S2): tR=7.722 min (m/z=260.1, 98.0% M+, BP).

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 588-96-5.

Reference:
Patent; Technische Universitaet Graz; Karl-Franzens-Universitaet Graz; Schweiger, Martina; Romauch, Matthias; Zimmermann, Robert; Mayer, Nicole; Breinbauer, Rolf; US9206115; (2015); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 588-96-5, name is p-Bromophenetole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: p-Bromophenetole

To a solution of 2R-allyl-3S-hydroxy-succinic acid diisopropylester (4.79 g, 18.5 MMOL), 4-bromo PHENETOLE (3.19 MI, 22.2 mmol, 1.2 eq. ) and NEt3 (6.22 ML, 44.6 MMOL, 2.4 eq. ) in CH3CN (40 ml), was added a sonicated (for 2 min) suspension of P (O-TOL) 3 (0.57 g, 2.22 mmol, 0.1 eq. ) and Pd (OAC) 2 (209 mg, 5%) in CH3CN (5 ML). The reaction mixture was heated to reflux for 2 hrs. CH3CN was removed under vacuum. The crude was extracted with AcOEt (3 X 200 ML), washed with water (50 mi) and with brine (50 ML). A purification by flash chromatography afforded the desired 2R- [3- (4-ethoxy-phenyl)-allyl]-3S- hydroxy-succinic acid diisopropyl ester (5.92 g, 84% yield). 1H-NMR ; delta (CDC13), 7.28 (2H, d, J = 8.8Hz), 6.83 (2H, d, J = 8.8Hz), 6.46 (1H, d, J = 15.7Hz), 6.02-6. 12 (1H, m), 4.98-5. 13 (2H, m), 4.26 (1H, dd, J = 7.1, 3. 0HZ), 4.02 (2H, q, J = 7. 0HZ), 3.23 (1H, d, J = 7. 1 HZ), 2.92-2. 97 (1H, m), 2.68-2. 79 (1H, m), 2.49-2. 62 (1H, m), 1.41 (3H, t, J=7.0 Hz) and 1.19- 1.30 (12H, m). LRMS: +ve ion 400 (M+Na).

The synthetic route of 588-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRITISH BIOTECH PHARMACEUTICALS LTD; LABORATOIRES SERONO S.A.; WO2004/101537; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 588-96-5, name is p-Bromophenetole, 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. Quality Control of p-Bromophenetole

A mixture of 4-bromophenetole (1.0 mmol), phenylboronic acid (1.2 mmol), organic solvents (6 mL), bases (2.0 mmol) and 0.5 mol % of catalyst was stirredat 80 C under air. After the reaction, the catalyst was separated by filtration. The filtrate was dried over Na2SO4 and filtered. The products were quantified by GC-MS analysis (Shimadzu GCMS-QP5050A equipped with a 0.25mm × 30 m DB-WAX capillary column). The typical GCMS analysis program was as follows: initial column temperature 100 C, hold 2 min, ramp temperature to 280 C at 15 C/min, and hold for 5 min.

The synthetic route of p-Bromophenetole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feng, Zhi-Qiang; Yang, Xiao-Li; Ye, Yuan-Feng; Hao, Lin-Yun; Bulletin of the Korean Chemical Society; vol. 35; 4; (2014); p. 1121 – 1127;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 588-96-5, 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. 588-96-5 name is p-Bromophenetole, 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.

Example I.1 (S)-N-(1-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide 147 mg (0.60 mmol) (S)-N-[1-(Piperidin-4-yl-phenyl)-ethyl]-acetamide (V.1) are added to a mixture of 100 mg (0.50 mmol) 1-bromo-4-ethoxy-benzene, 197 mg (2.00 mmol) sodium tert-butyrat, 59 mg (0.20 mmol) 2-(di-tert-butylphosphino)biphenyl and 46 mg (0.05 mmol) tris-(dibenzylidenaceton)-dipalladium(0) in 2.0 mL 1,4-dioxane. The mixture is stirred for 4 h at 45 C. After that time, the mixture is filtered over celite. The solvent is removed in vacuo from the filtrate. The residue is purified by HPLC (column: Waters XBridge 5 muM; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product. C23H30N2O2 (M=366.5 g/mol) ESI-MS: 367 [M+H]+

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/157425; (2012); A1;,
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. 588-96-5, name is p-Bromophenetole, A new synthetic method of this compound is introduced below., Quality Control of p-Bromophenetole

General procedure: CS127 was prepared using a modified literature procedure [16]. A solution of butyllithium (1. hexane, 0.15 mL) was added to a solution of 4-bromotoluene (8.52 mg, 0.050 mmol) in hexane (15 mL). After stirring for 1 h, N,N’-diisopropylcarbodiimide (6.29 mg, 0.050 mmol) was added dropwise. The solution was stirred for 1 h at room temperature and then the dimer [(FMeppy)2Ir(mu-Cl)]2 (30 mg, 0.025 mmol) was added. The mixture was heated overnight at 70 C. After being cooled to room temperature, the resulting precipitate was collected and washed with diethyl ether. The dried product was obtained as a yellow powder. Yield 65%.

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; Sahin, Cigdem; Goren, Aysen; Varlikli, Canan; Journal of Organometallic Chemistry; vol. 772; (2014); p. 68 – 78;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 588-96-5, name is p-Bromophenetole, 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 588-96-5, Safety of p-Bromophenetole

General procedure: In air, aryl halide (0.2 mmol), arylboronic acid (0.22 mmol),K2CO3 (0.3 mmol), 5 ml of distilled water, and 2 mg of catalystwere combined in a 10 ml round bottom flask. The reactionmixture was magnetically stirred and the temperature wasmaintained at 75 C in an oil bath. Reaction progress was monitoredby TLC. After reaction was completed, the reaction mixturewas cooled to room temperature and filtrated. The filtratedsolid was washed with water (35 ml) and dissolved withethyl acetate. The catalyst was separated by filtration, washedwith water, and dried in vacuum. The combined organic phasewas dried with anhydrous MgSO4, and the solvent was removedunder reduced pressure to give the product.

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, p-Bromophenetole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ma, Hengchang; Bao, Zhikang; Han, Guobin; Yang, Ningning; Xu, Yufei; Yang, Zengming; Cao, Wei; Ma, Yuan; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 34; 3; (2013); p. 578 – 584;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 588-96-5, name is p-Bromophenetole, 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. COA of Formula: C8H9BrO

General procedure: CS127 was prepared using a modified literature procedure [16]. A solution of butyllithium (1. hexane, 0.15 mL) was added to a solution of 4-bromotoluene (8.52 mg, 0.050 mmol) in hexane (15 mL). After stirring for 1 h, N,N’-diisopropylcarbodiimide (6.29 mg, 0.050 mmol) was added dropwise. The solution was stirred for 1 h at room temperature and then the dimer [(FMeppy)2Ir(mu-Cl)]2 (30 mg, 0.025 mmol) was added. The mixture was heated overnight at 70 C. After being cooled to room temperature, the resulting precipitate was collected and washed with diethyl ether. The dried product was obtained as a yellow powder. Yield 65%.

The synthetic route of p-Bromophenetole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sahin, Cigdem; Goren, Aysen; Varlikli, Canan; Journal of Organometallic Chemistry; vol. 772; (2014); p. 68 – 78;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 588-96-5 as follows. Recommanded Product: p-Bromophenetole

Step 1:Magnesium (8.24 g, 0.339 mol) was added to 300 mL of tetrahydrofuran (THF) in a reactor substituted with nitrogen atmosphere and dissolved by stirring. While keeping the internal temperature at 20 to 30 C, 4-bromophenetol 62 g, 0.308 mol) and 220 mL of tetrahydrofuran was slowly added thereto. After completion of the addition, the internal temperature was raised to 40 to 45 C and stirred for 2 hours. Step 2: In a reactor substituted with nitrogen atmosphere, (S)-tert-butyl 2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)aziridine-1-carboxylate (50 g, 0.206 mol) was added to 50 mL of toluene and dissolved with stirring, and CuBrS(CH3)2 (0.4 g, 0.002 mol) was added thereto. The internal temperature was further stirred for 30 minutes while maintaining the internal temperature at 20 to 25 C,and the internal temperature was cooled to -40 C.The solution of 4-bromophenetol magnesium bromide prepared according to the above step 1 was slowly added while keeping the internal temperature at -40 C or lower.After completion of the addition, the internal temperature was raised to -30 to -20 C and stirred for 1 hour. When the reaction was complete, 400 mL of 10% acetic acid aqueous solution and 400 mL of toluene were added to quench and separate.The separated oil layer was washed with 400 mL of a 7% sodium Sodium bicarbonate aqueous solution and 400 mL of purified water, and Sodium sulfate was added to dehydrate and then filtered.Thereafter, the filtrate was concentrated, 150 mL of methanol was added to the concentrated residue, stirred at an internal temperature of 20 to 25 C for 1 hour, and then filtered. The filtrate was concentrated again to give 75.1 g of the title compound tert-butyl (1S)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-ethoxyphenyl)ethylcarbamate yield: 100 %

According to the analysis of related databases, 588-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eseuti Pam Co., Ltd.; Kim Yeong-hun; Oh Jun-hyeon; Kang Sang-gyu; Jang Sun-gi; Im Geun-jo; (14 pag.)KR2018/50091; (2018); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 588-96-5 as follows. Safety of p-Bromophenetole

General procedure: In air, aryl halide (0.2 mmol), arylboronic acid (0.22 mmol),K2CO3 (0.3 mmol), 5 ml of distilled water, and 2 mg of catalystwere combined in a 10 ml round bottom flask. The reactionmixture was magnetically stirred and the temperature wasmaintained at 75 C in an oil bath. Reaction progress was monitoredby TLC. After reaction was completed, the reaction mixturewas cooled to room temperature and filtrated. The filtratedsolid was washed with water (35 ml) and dissolved withethyl acetate. The catalyst was separated by filtration, washedwith water, and dried in vacuum. The combined organic phasewas dried with anhydrous MgSO4, and the solvent was removedunder reduced pressure to give the product.

According to the analysis of related databases, 588-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ma, Hengchang; Bao, Zhikang; Han, Guobin; Yang, Ningning; Xu, Yufei; Yang, Zengming; Cao, Wei; Ma, Yuan; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 34; 3; (2013); p. 578 – 584;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 588-96-5, name is p-Bromophenetole, 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 588-96-5, Safety of p-Bromophenetole

To a solution of tert-butyl 4-(piperazinyisulfonyl)perhydro-2H-pyran-4-carboxyate (715 mg, 2.14 mmol, supplied by CarboGen) in toluene (15 mL) under N2 were added 1-bromo-4-ethoxybenzene (473 mg, 2.35 mmol), sodium tert-butoxide (514 mg, 5.35 mmol), palladium(II) acetate (5.0 mg, 0.021 mmol), and tri-tert-butylphosphine (3.5 mg, 0.17 mmol). The reaction was continued overnight at 60 C. under N2. No starting material remained at this time, so the reaction mixture was diluted with methanol and concentrated under reduced pressure. The residue was partially dissolved in dichloromethane and filtered. The filtrate was concentrated under reduced pressure, and the resulting dark material was triturated with diethyl ether to produce a white solid, which was collected by suction filtration to produce 640 mg of clean product (66%). 1H NMR and mass spectrometry (MH+=455) were consistent with the desired structure.

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; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem