Category: 588-96-5

588-96-5, name is p-Bromophenetole, belongs to ethers-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. Quality Control of p-Bromophenetole

Preparation Example 3 Synthesis of 1-bromo-3-(4-ethoxybenzyl)benzene; A 2.6 M n-butylithium hexane solution (5.8 mL) was added to a mixture of 4-bromophenetole (2.87 g, 0.0143 mol) and tetrahydrofuran (30 mL) at -78C. After the mixture was stirred for 0.5 hours, a tetrahydrofuran (15 mL) solution of 3-bromobenzaldehyde (2.65 g, 0.0143 mol) was added, and further stirred for 15 minutes to warm the reaction mixture to room temperature. After the reaction mixture was added with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=7:1 to 5:1) to obtain colorless oily (3-bromophenyl)(4-ethoxyphenyl)methanol (3.94 g, 90%). Then, Et3SiH (4.09 mL, 0.0256 mol) and BF3·Et2O (1.47 mL, 0.0116 mol) were added sequentially to a chloroform (22 mL) solution of (3-bromophenyl)(4-ethoxyphenyl)methanol (3.92 g, 0.0128 mol) at -60C. After stirred for one hour, the reaction solution was warmed to room temperature. After the reaction mixture was added with a saturated sodium carbonate aqueous solution and extracted with chloroform, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to obtain a colorless oily title compound (2.84 g, 76%). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.40 (t, J=7.0 Hz, 3 H) 3.88 (s, 2 H) 4.01 (q, J=7.0 Hz, 2 H) 6.83 (d, J=8.9 Hz, 2 H) 7.07 (d, J=8.9 Hz, 2 H) 7.09 – 7.18 (m, 2 H) 7.29 – 7.34 (m, 2 H).

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

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1845095; (2007); A1;,
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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. name: 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;,
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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, Application In Synthesis 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;,
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588-96-5, name is p-Bromophenetole, belongs to ethers-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. Safety of p-Bromophenetole

Example XIV.1 2-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-propionic acid 1.00 g (4.04 mmol) 2-(4-Piperidin-4-yl-phenyl)-propionic acid methyl ester (XI.3) are added to a mixture of 813 mg (4.04 mmol) 1-bromo-4-ethoxy-benzene, 1.60 g (97%, 16.2 mmol) sodium tert-butyrat, 483 mg (1.62 mmol) 2-(di-tert-butylphosphino)biphenyl and 370 mg (0.40 mmol) tris-(dibenzylidenaceton)-dipalladium(0) in 10 mL 1,4-dioxane. The mixture is stirred for 12 h at 70 C. After that time, the precipitate is filtered off and washed with ACN and diethyl ether. The residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product. C22H27NO3 (M=353.5 g/mol) ESI-MS: 354 [M+H]+Rt (HPLC): 1.69 min (method C)

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

Reference:
Patent; ROTH, Gerald Juergen; FLECK, Martin; LEHMANN-LINTZ, Thorsten; NOSSE, Bernd; US2013/143876; (2013); A1;,
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588-96-5, A common heterocyclic compound, 588-96-5, name is p-Bromophenetole, molecular formula is C8H9BrO, 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: b.Cyanation of aryl bromides. To a solution of arylbromide (0.5 mmol) in EtOH (5.0 mL) was added NCTS (272 mg, 1.0 mmol), PdCl2 (13.3 mg, 0.075 mmol), and Ag2O (57.75 mg, 0.5 mmol). The mixture was stirred at 70 for 24 hunder air atmosphere. Then the reaction mixture was cooled to room temperature and filtered through a pad of celite (1.0 g) and rinsed with CH2Cl2 (10.0 mL). The resulting organic solution was concentrated under reduced pressure and further purified by flash chromatography (SiO2,petroleum ether/EtOAc gradient), yielding the corresponding aryl nitriles.

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

Reference:
Article; Li, Jizhen; Xu, Wenbin; Ding, Junshuai; Lee, Kuo-Hsiung; Tetrahedron Letters; vol. 57; 11; (2016); p. 1205 – 1209;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

588-96-5, name is p-Bromophenetole, belongs to ethers-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. Safety of p-Bromophenetole

General procedure: The Teflon-lined sealed tube (20 mL) was charged with a 1,4-dioxane solution of sodium fluoroalkoxide RFONa [freshly prepared from fluoroalkanol RFOH (3.3(n + 1) mmol) and Na (3.0 (n + 1) mmol) in 1,4-dioxane (5 mL)], unactivated arylbromide ArBrn (3.0 mmol), CuBr (0.3n mmol) and DMF (3.0n mmol). The sealed tube was heated to 110 C and stirred for 6 h. After the completion of reaction, the concentration of the mixture in vacuo gave a residue, to which was added methyl tert-butyl ether (MTBE, 20 mL) and diluted hydrochloric acid (10 mL, 1.0 mol/L). The organic phase was separated, and the aqueous phase was extracted with MTBE (10 mL 9 3). The combined organic layer was dried over anhydrous MgSO4, andthen concentrated in vacuo to supply a crude product. Lastly, the purification of the crude product provided the desired product via column chromatography on silica gel (eluents: petroleum ether/ethyl acetate 20:1).

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

Reference:
Article; Guo, Ying; Li, Yu-Dao; Chen, Cheng; Zhao, Jian-Hong; Liu, Hong-Wei; Liao, Dao-Hua; Ji, Ya-Fei; Research on Chemical Intermediates; vol. 42; 3; (2016); p. 2525 – 2537;,
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Some common heterocyclic compound, 588-96-5, name is p-Bromophenetole, molecular formula is C8H9BrO, 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. Product Details of 588-96-5

To a solution of 4-bromophenetole (1.86 mL, 13.0 mmol) in anhydrous THF (15 mL) was added dropwise (over a 5-min period) a solution of n-BuLi (6.0 mL, 2.5 M in hexane) under nitrogen atmosphere at -78 C. The resulting mixture was stirred at -78 C for 1 hour, and then a solution of the Weinreb amide 43 (1.85 g, 10.0 mmol) in anhydrous THF (5.0 mL) was added dropwise (over a 10-min period). The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. The mixture was poured into a 1 M HC1 solution (25 mL) and extracted with EtOAc (50 mL). The organic phase was subsequently washed with brine, dried over MgS04 and evaporated under vacuum. The residue was further purified by silica column chromatography (Biotage) to provide (4- ethoxyphenyl)(3-methylthiophen-2-yl)methanone (44, 1.52 g, 6.16 mmol, 62 %). NMR (400 MHz, CDC13) delta 7.84 (d, J = 8.8 Hz, 2H), 7.45 (d, J = 5.2 Hz, 1H), 7.98 (d, J = 4.8 Hz, 1H), 6.94 (d, J – 9.2 Hz, 2H), 4.1 1 (q, J = 6.8 Hz, 2H), 2.40 (s, 3H), 1.45 (t, J= 6.8 Hz, 3H); MH+ 247.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 588-96-5, its application will become more common.

Reference:
Patent; GREEN CROSS CORPORATION; LEE, Jinhwa; SONG, Kwang-Seop; LEE, Suk Ho; WO2012/33390; (2012); A2;,
Ether – Wikipedia,
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Synthetic Route 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.

General procedure: A 15 mL screw cap test tube was charged with Cu(OAc)2*H2O (20 mg, 0.1 mmol, 2 mol %), L4 (78 mg, 0.4 mmol, 8 mol %), hexane-2,5-dione (46 mg, 0.4 mmol, 8 mol %), KOH (650 mg, 10 mmol, 200 mol %), adipic acid (219 mg, 1.5 mmol, 30 mol %), NaOAc (246 mg, 3 mmol, 60 mol %), CTAB (182 mg, 0.5 mmol, 10 mol %), H2O (0.5 mL), aryl bromide (5 mmol) and amine (6.5 mmol, 130 mol %). Argon (flow rate 5-7 mL/min) was bubbled through the resulting mixture for 5 min. The reaction mixture was stirred in a closed test tube at 100C for 3-4 h until complete consumption of starting material as monitored by TLC (eluent-hexane), then cooled to room temperature and diluted with EtOAc (30 mL). The EtOAc solution was purified by flash-chromatography, washed with water (310 mL), and dried with anhydrous Na2SO4. Then EtOAc was evaporated under reduced pressure and the residue was recrystallized from hexane (substances 1-4) or aq EtOH (substances 5-9). In a case of the substances 5, 7-9 the residue was dissolved in diethyl ether. Aq HCl (37%) was added dropwise to the resulting solution until pH 3-4. The formed precipitate was filtered, washed with diethyl ether (10 mL) and dried at 50 C.

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:
Article; Kurandina; Eliseenkov; Khaibulova; Petrov; Boyarskiy; Tetrahedron; vol. 71; 41; (2015); p. 7931 – 7937;,
Ether – Wikipedia,
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Reference of 588-96-5, A common heterocyclic compound, 588-96-5, name is p-Bromophenetole, molecular formula is C8H9BrO, 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.

Example XII.1 (S)-(1-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-ethyl)-carbamic acid tert-butyl ester 6.21 g (19.1 mmol) cesium carbonate are added to a mixture of 5.80 mg (19.1 mmol) (S)-[1-(4-piperidin-4-yl-phenyl)-ethyl]-carbamic acid tert-butyl ester (V.5), 4.21 g (21.0 mmol) 1-bromo-4-ethoxy-benzene, 454 mg (0.953 mmol) X-Phos and 214 mg (0.953 mmol) palladium(II) acetate in 50 mL toluene/10 mL tert-butanol. The mixture is stirred for 3 h at 120 C. under inert gas atmosphere. After that time, the mixture is poured into water and extracted with ethyl acetate. The organic layer is washed with water and dried over magnesium sulphate. The solvent is removed in vacuo and the residue is recrystallized from acetonitrile. C26H36N2O3 (M=424.6 g/mol) ESI-MS: 425 [M+H]+

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/157425; (2012); A1;,
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

To a solution of 2R-allyl-3S-hydroxy-succinic acid diisopropylester (4.79 g, 18.5 MMOL), 4-bromo phenetole (3.19 ML, 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 vacuo. The crude was extracted with AcOEt (3 X 200 ML), washed with water (50 ML) 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).

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; VERNALIS (OXFORD) LIMITED; LABORATOIRES SERONO S.A.; WO2005/19194; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem