Category: 5414-19-7

Application of 5414-19-7, 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. 5414-19-7 name is 1-Bromo-2-(2-bromoethoxy)ethane, 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.

Step 1: Ethyl 4-(4-bromophenyl)tetrahydro-2H-pyran-4-carboxylate 6.0 g (24.7 mmol) of ethyl 4-bromophenylacetate were dissolved in 120 ml of abs. DMF under argon, 1.48 g (37.0 mmol, 60% strength) of sodium hydride were added, while cooling in an ice bath, and the mixture was stirred for 30 min. 5.72 g (24.7 mmol) of bis(2-bromoethyl)ether were then added, while constantly cooling in an ice bath, and the mixture was stirred at approx. 0 C. for 1 h. After renewed addition of 1.48 g of 60% strength sodium hydride, the mixture was stirred again for 1 h, while cooling in an ice bath. Saturated aqueous ammonium chloride was then added and the mixture was extracted with ethyl acetate. The organic phase was washed with water and with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated on a rotary evaporator. The residue was purified by column chromatography over silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 2.62 g (33% of th.) of the title compound were obtained. 1H-NMR (400 MHz, CDCl3, delta/ppm): 7.47 (d, 2H), 7.25 (d, 2H), 4.14 (q, 2H), 3.93 (dt, 2H), 3.56 (td, 2H), 2.59 (dd, 2H), 1.93 (m, 2H), 1.19 (t, 3H). MS (DCI, NH3): m/z=329 [M+NH4]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-(2-bromoethoxy)ethane, and friends who are interested can also refer to it.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; Haerter, Michael; Beck, Hartmut; Ellinghaus, Peter; Berhoerster, Kerstin; Greschat, Susanne; Thierauch, Karl-Heinz; Suessmeier, Frank; US2013/196964; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 5414-19-7, A common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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.

Step 1 Preparation of 4-(4-(trifluoromethyl) phenyl)-tetrahydro-2H-pyran-4-carbonitrile To a stirred solution of 2-(4-(trifluoromethyl)phenyl)acetonitrile (2.0 g, 10.8 mmol) in DMF (10 mL) was slowly added a suspension of NaH (60%, 0.95 g, 23.7 mmol) in DMF (10 mL) at 0 C. under N2 atmosphere over 10 min, the reaction was allowed to warm to room temperature and stirred for 0.5 h. Then the reaction was cooled to 0 C. and 2,2′-dibromodiethyl ether (1.5 mL, 11.8 mmol) in DMF (20 mL) was added dropwise over 60 min. The reaction was allowed to warm to room temperature and stirred for 1 h. The mixture was quenched with water (30 mL) and extracted with EtOAc (30 mL*3). The combined organic layer was washed with water (10 mL) and brine (10 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified with column chromatography on silica gel (petroleum ether_EtOAc=100:1) to afford 4-(4-(trifluoromethyl)phenyl)-tetrahydro-2H-pyran-4-carbonitrile (2.30 g, 83%) as red oil. GC-MS: [M]+ 255; tR=10.39 min.

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; KARRA, Srinivasa R.; (153 pag.)US2016/168090; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 5414-19-7,Some common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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: Dimethyl 5-hydroxyisophthalate (1, 6 mmol), 1,omega-dialkylating agent (18 mmol) and K2CO3 (60 mmol) were stirred in anhydrous DMF (60 mL) at a room temperature for 18 h. The reaction mixture was Celite filtered, washed with dichloromethane and toluene. The combined filtrates were evaporated to dryness and the residual colorless oil was chromatographed (dichloromethane, then dichloromethane:methanol, 100:1, v/v) to give a crude product which was a white solid. The yields ranged from 18 to 80%. Some reactants prepared as above have been obtained previously by diverse methods: dimethyl 5-(2-bromoethoxy)isophthalate (2a) [11], dimethyl 5-(5-bromopentoxy)isophthalate (2b) [12] and dimethyl 5-(3-bromopropoxy)isophthalate (2d) [13].

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-2-(2-bromoethoxy)ethane, its application will become more common.

Reference:
Article; Gierszewski, Mateusz; Falkowski, Michal; Sobotta, Lukasz; Stolarska, Magdalena; Popenda, Lukasz; Lijewski, Sebastian; Wicher, Barbara; Burdzinski, Gotard; Karolczak, Jerzy; Jurga, Stefan; Gdaniec, Maria; Tykarska, Ewa; Sikorski, Marek; Mielcarek, Jadwiga; Goslinski, Tomasz; Journal of Photochemistry and Photobiology A: Chemistry; vol. 307-308; (2015); p. 54 – 67;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 5414-19-7,Some common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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: Dimethyl 5-hydroxyisophthalate (1, 6 mmol), 1,omega-dialkylating agent (18 mmol) and K2CO3 (60 mmol) were stirred in anhydrous DMF (60 mL) at a room temperature for 18 h. The reaction mixture was Celite filtered, washed with dichloromethane and toluene. The combined filtrates were evaporated to dryness and the residual colorless oil was chromatographed (dichloromethane, then dichloromethane:methanol, 100:1, v/v) to give a crude product which was a white solid. The yields ranged from 18 to 80%. Some reactants prepared as above have been obtained previously by diverse methods: dimethyl 5-(2-bromoethoxy)isophthalate (2a) [11], dimethyl 5-(5-bromopentoxy)isophthalate (2b) [12] and dimethyl 5-(3-bromopropoxy)isophthalate (2d) [13].

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-2-(2-bromoethoxy)ethane, its application will become more common.

Reference:
Article; Gierszewski, Mateusz; Falkowski, Michal; Sobotta, Lukasz; Stolarska, Magdalena; Popenda, Lukasz; Lijewski, Sebastian; Wicher, Barbara; Burdzinski, Gotard; Karolczak, Jerzy; Jurga, Stefan; Gdaniec, Maria; Tykarska, Ewa; Sikorski, Marek; Mielcarek, Jadwiga; Goslinski, Tomasz; Journal of Photochemistry and Photobiology A: Chemistry; vol. 307-308; (2015); p. 54 – 67;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 5414-19-7, A common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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 t-butyl ester from Part D (3 g, 6.2 mmol), N,N-Dimethylformamide (15 mL), K2CO3 (2.76 g, 20 mmol), 2-bromoethyl ether, Aldrich, (1.75 g, 7.6 mmol), and 18-Crown-6 (0.49 g, 1.86 mmol) were heated together at 65 C. under an N2 atmosphere overnight. An additional 1 g of K2CO3 (7.2 mmol) and 0.87 g of 2-bromoethyl ether (3.78 mmol) were added to the mixture, and it was again stirred overnight at 65 C. under an N2 atmosphere. The reaction mixture was cooled to ambient temperature, and then added to deionized water (75 mL) and ethyl acetate (200 mL). The layers were separated, and the aqueous layer was back-extracted with ethyl acetate (50 mL). The combined ethyl acetate layers were washed with 100 mL of each of a 1:1 mixture of deionized water:saturated NaCl(aq) and saturated NaCl(aq), dried over MgSO4, filtered, and concentrated in vacuo. Chromatography (on silica, ethyl acetate/hexanes) produced 1.76 g (51.24%) a t-butyl ester pyran in the form of a solid.

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 5414-19-7, These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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.

A solution of 2-(4-phenylthiazol-2-yl)acetonitrile (0.84 g, 4.19 mmol) in THF (25 mL) was cooled to 0 C. NaH was added (0.5 g, 60% dispersion in oil) portionwise over 10 min. The resulting mixture was allowed to warm up to room temperature and stirred for 20 min. 2-Bromoethyl ether (1.58 mL, 12.5 mmol) was added dropwise. The reaction mixture was further stirred at room temperature for 1 h and then quenched with saturated NH4Cl solution. The reaction mixture was diluted with EtOAc and the organic layer was washed with H2O and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60-120 mesh, eluent 4-8% EtOAc in petroleum ether) to afford 4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-carbonitrile (0.97 g, yield 85%) as a yellow solid: 1H NMR (300 MHz, CDCl3) delta 7.91-7.94 (m, 2H), 7.51 (s, 1 H), 7.37-7.48 (m, 3H), 4.07-4.14 (m, 2H), 3.87-3.96 (m, 2H), 2.32-2.43 (m, 4H). MS (ESI) m/z: Calculated for C15H14N2OS: 270.08; found: 271.2 (M+H)+.

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tempero Pharmaceuticals, Inc.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby; EP2533783; (2015); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 5414-19-7, 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows.

The product of Part F (5.0 g, 10.6 mmol), 18-crown-6 (Aldrich, 0.5 g, catalytic amount), potassium carbonate (Aldrich, 4.4 g, 31.8 mmol), and bis(bromoethyl)ether (Aldrich, 4.9 g, 21.2 mmol) were slurried in N,N-dimethylformamide (20 ml) and stirred at 65 C. for 15 hr. Afterward, the mixture was diluted with water (50 ml) and extracted with ethyl acetate (3?100 ml). The organics were combined and washed with water (twice), washed with brine (twice), dried over Na2SO4, and concentrated for a tan oil. The oil was washed with hexanes, and then dried to afford a tan oil. The tan oil was recrystallized from methanol to afford the desired intermediate in the form of a white solid (2.5 g, 44% yield). 1H NMR and LCMS showed desired intermediate.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-(2-bromoethoxy)ethane. I believe this compound will play a more active role in future production and life.

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

Reference of 5414-19-7, The chemical industry reduces the impact on the environment during synthesis 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, I believe this compound will play a more active role in future production and life.

To a room temperature mixture of the tert-butyl [2- [ (4-BROMOPHENYL) SULFONYL]] acetate (2) from Part A (0.25 mol) in 100 mL dimethyl formamide (“DMF”) was added 18-crown-6 (19.4 g, 0.07 mol), potassium carbonate [(“K2CO3”)] (169 g, 1.22 mol), and bis (2- bromoethyl) ether (62.5 g, 0.27 mol). The mixture was stirred at room temperature for 18 hr, after which time no starting material (2) was detected by HPLC. The resulting mixture was concentrated, diluted in 500 mL ethylacetate [(“CH3COOC2HS”OR”ETOAC”),] and filtered. The resulting filtrate was concentrated to produce a yellow oil that solidified upon standing to afford the desire product (3). LCMS: [M+Na] = 427.05.

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-2-(2-bromoethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/811; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 5414-19-7, 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of the ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate (500 mg, 2.95 mmol), C52CO3 (2.9 g, 8.87 mmol), 1-bromo-2-(2-bromoethoxy) ethane (1.37 g, 5.90 mmol) in DMA(lOmL) as stirred at 120C overnight. Then H20 (20 mL) was added to the mixture and it was extracted with EA(x3). The organic layer was dried and purified by flash to give desired compound as yellow oil (610 mg, 87%). ESI-MS m/z: 240.0 [M+Hjt

The synthetic route of 1-Bromo-2-(2-bromoethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; OR, Yat, Sun; (434 pag.)WO2017/15449; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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 5414-19-7, Recommanded Product: 1-Bromo-2-(2-bromoethoxy)ethane

A solution of ethyl 3-aminothieno[2,3-bjpyridine-2-carboxylate (500 mg, 2.25 mmol), 1-bromo-2-(2-bromoethoxy)ethane (1.38 g, 6 mmol) and Cs2CO3 (1.63 g, 5 mmol) in DMA (30mL) was stirred for 3 hours at 80C. H20 (50 mL) was added and it was extracted withEA(3x). The organic layer was concentrated and purified by reverse phase C18 columnchromatography (MeCN/H20) to give desired compound as light brown oil. (500 mg, 76 %). ESI-MS m/z: 293.2 [M+Hf

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-2-(2-bromoethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; OR, Yat, Sun; (434 pag.)WO2017/15449; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem