Category: 37746-78-4

Synthetic Route of 37746-78-4,Some common heterocyclic compound, 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, molecular formula is C6H9BrO2, 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 6 N NaOH (0.1 mL) solution was added dropwise into a solution of 13 (100 mg, 0.38 mmol) and 30% H2O2 (0.05 mL) in EtOH (5 mL) at 0 C. The reaction mixture which resulted, was stirred for 2 h at the same temperature after which water was added to the reaction mixture and it was extracted with CH2Cl2 (2 * 10 mL). The combined organic extracts were washed with brine (2 * 15 mL). The organic layer was dried (MgSO4) and concentrated under vacuum to yield the crude epoxide ethyl ester. The crude compound was purified by flash column chromatography (10% EtOAc in hexanes) on silica gel to afford epoxide ethyl ester 29 (55 mg, 52%). 1H NMR (300 MHz, CDCl3): delta 7.99 (d, J = 8.4 Hz, 2H), 7.55 (d, J = 8.4 Hz, 2H), 4.46 (d, J = 1.8 Hz, 1H), 4.32 (m, 2H), 3.70 (d, J = 1.8 Hz, 1H), 1.38 (m, 12H); 13C NMR (75 MHz, CDCl3): delta 191.3, 167.31, 158.5, 132.5, 128.6, 126.0, 62.3, 55.2, 53.0, 35.3, 31.0, 14.1. HRMS (ESI) (M+Na)+, calcd for C16H20O4Na 299.1259; found 299.1248.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (E)-Ethyl 4-bromobut-2-enoate, its application will become more common.

Reference:
Article; Tiruveedhula, V.V.N. Phani Babu; Witzigmann, Christopher M.; Verma, Ranjit; Kabir, M. Shahjahan; Rott, Marc; Schwan, William R.; Medina-Bielski, Sara; Lane, Michelle; Close, William; Polanowski, Rebecca L.; Sherman, David; Monte, Aaron; Deschamps, Jeffrey R.; Cook, James M.; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7830 – 7840;,
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Ester – an overview | ScienceDirect Topics

Application of 37746-78-4, These common heterocyclic compound, 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, 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: A solution of TMSCl (3 mol%) in anhyd 1,4-dioxane (1 mL) wasadded to a suspension of Zn dust (2 equiv) in anhyd 1,4-dioxane(3 mL), and the resulting suspension was refluxed with vigorousstirring for 25 min. The appropriate nitrile (2 mmol) in dry 1,4-dioxane (1 mL) and ethyl (E)-4-bromobut-2-enoate (12; 2equiv) in dry 1,4-dioxane (1 mL) were simultaneously addeddropwise to the refluxing suspension during 10 min by usingtwo syringes. The resulting light-green mixture was refluxeduntil all the starting material was consumed and the colorchanged to brown (TLC; 3-6 h). The mixture was cooled to r.t.then centrifuged (700 rpm). The upper solution was decantedand the remaining solid was washed with 1,4-dioxane (4 ¡Á 1mL). The 1,4-dioxane solutions were combined and concentratedto about 1 mL under reduced pressure in a rotatory evaporator.The residue was treated with 50% aq K2CO3 until the pHreached 13 (~5 mL). The resulting mixture was stirred for 30min at r.t. (30 C) then diluted with CH2Cl2 (10 mL) and H2O (10mL). The organic layer was separated, washed sequentially withH2O (2 ¡Á 10 mL) and brine (10 mL), dried (Na2SO4), and evaporatedunder reduced pressure to give a crude product that waspurified by column chromatography [silica gel (100-200 mesh);15-60% EtOAc-hexane].6-Phenylpyridin-2(1H)-one (13a)By following the general procedure, the reaction of PhCN (5a;201 mg, 1.94 mmol) with crotonate 12 (374 mg, 1.94 mmol) inthe presence of Zn (252 mg, 3.88 mmol) and TMSCl (7 mg, 3 mol%) in 1,4-dioxane (6 mL) for 4 h, followed by hydrolysis with 50%aq K2CO3 (5 mL) gave a light-yellow solid; yield: 205 mg (62%);mp 194-195 C; Rf = 0.5 (hexanes-EtOAc, 2:1).IR (KBr): 2904, 1643, 1612, 1550, 1493, 990, 921, 795, 761 cm-1.1H NMR (400 MHz, CDCl3): delta = 12.49 (br s, 1 H), 7.72 (d, J = 6.9Hz, 2 H), 7.59-7.40 (m, 4 H), 6.55-6.47 (m, 2 H). 13C NMR (100MHz, CDCl3): delta = 165.4, 147.1, 141.5, 133.6, 130.1, 129.2, 126.8,118.7, 105.0. HRMS (ESI): m/z [M + H] calcd for C11H9NO:172.0762; found: 172.0750.

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rao, H. Surya Prakash; Muthanna, Nandurka; Padder, Ashiq Hussain; Synlett; vol. 29; 12; (2018); p. 1649 – 1653;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H9BrO2

General procedure: A solution of TMSCl (3 mol%) in anhyd 1,4-dioxane (1 mL) wasadded to a suspension of Zn dust (2 equiv) in anhyd 1,4-dioxane(3 mL), and the resulting suspension was refluxed with vigorousstirring for 25 min. The appropriate nitrile (2 mmol) in dry 1,4-dioxane (1 mL) and ethyl (E)-4-bromobut-2-enoate (12; 2equiv) in dry 1,4-dioxane (1 mL) were simultaneously addeddropwise to the refluxing suspension during 10 min by usingtwo syringes. The resulting light-green mixture was refluxeduntil all the starting material was consumed and the colorchanged to brown (TLC; 3-6 h). The mixture was cooled to r.t.then centrifuged (700 rpm). The upper solution was decantedand the remaining solid was washed with 1,4-dioxane (4 ¡Á 1mL). The 1,4-dioxane solutions were combined and concentratedto about 1 mL under reduced pressure in a rotatory evaporator.The residue was treated with 50% aq K2CO3 until the pHreached 13 (~5 mL). The resulting mixture was stirred for 30min at r.t. (30 C) then diluted with CH2Cl2 (10 mL) and H2O (10mL). The organic layer was separated, washed sequentially withH2O (2 ¡Á 10 mL) and brine (10 mL), dried (Na2SO4), and evaporatedunder reduced pressure to give a crude product that waspurified by column chromatography [silica gel (100-200 mesh);15-60% EtOAc-hexane].

According to the analysis of related databases, 37746-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rao, H. Surya Prakash; Muthanna, Nandurka; Padder, Ashiq Hussain; Synlett; vol. 29; 12; (2018); p. 1649 – 1653;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

General procedure: To a vigorously stirring solution of alpha-imino ester 1 (0.5 mmol,1 equiv) and E-ethyl-4-bromocrotonate or methyl-4-bromocrotonate (2, 1.5 mmol, 3 equiv) in EtOH (2 mL) was added indium powder (1 mmol, 2 equiv). The mixture was allowed to stir vigorously for 6 h at 30 C. After this period, the reaction mixturewas quenched with 2 mL of water and transferred to a separating funnel and extracted using ethyl acetate (315 mL). The combined organic layers were dried over anhydrous Na2SO4. Then the solvent was evaporated under vacuum. Purification of the resulting crude reaction mixture by column chromatography on silica gel (EtOAc/Hexane as eluent) gave the product 3 (see Tables 1 and 2 and Scheme 2 for individual entries).

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aslam, Nayyar Ahmad; Babu, Srinivasarao Arulananda; Sudha, Arya Jayadev; Yasuda, Makoto; Baba, Akio; Tetrahedron; vol. 69; 32; (2013); p. 6598 – 6611;,
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Ester – an overview | ScienceDirect Topics

Application of 37746-78-4, The chemical industry reduces the impact on the environment during synthesis 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, I believe this compound will play a more active role in future production and life.

Into a 10-L 4-necked round-bottom flask was placed 2-bromo-4-fluorophenol (500 g, 2.62 mol, 1.00 equiv), N,N-dimethylformamide (5 L), potassium carbonate (1253 g, 9.07 mol, 3.46 equiv), and ethyl (2E)-4-bromobut-2-enoate (1010 g, 5.23 mol, 2.00 equiv). The resulting solution was stirred for 12 h at room temperature. The solids were collected by filtration. The reaction was then quenched by the addition of 15 L of water and extracted with 3×10 L of ethyl acetate. The organic layers were combined and washed with 4×20 L of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/20). The collected fractions were combined and concentrated under vacuum to give 500 g (63%) of ethyl (2E)-4-(2-bromo-4-fluorophenoxy)but-2-enoate (5) as a white solid.

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, (E)-Ethyl 4-bromobut-2-enoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTUATE THERAPEUTICS INC.; ZHANG, Yamin; (72 pag.)WO2019/32958; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

37746-78-4, A common compound: 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: To a vigorously stirring solution of alpha-imino ester 1 (0.5 mmol,1 equiv) and E-ethyl-4-bromocrotonate or methyl-4-bromocrotonate (2, 1.5 mmol, 3 equiv) in EtOH (2 mL) was added indium powder (1 mmol, 2 equiv). The mixture was allowed to stir vigorously for 6 h at 30 C. After this period, the reaction mixturewas quenched with 2 mL of water and transferred to a separating funnel and extracted using ethyl acetate (315 mL). The combined organic layers were dried over anhydrous Na2SO4. Then the solvent was evaporated under vacuum. Purification of the resulting crude reaction mixture by column chromatography on silica gel (EtOAc/Hexane as eluent) gave the product 3 (see Tables 1 and 2 and Scheme 2 for individual entries).

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, (E)-Ethyl 4-bromobut-2-enoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Aslam, Nayyar Ahmad; Babu, Srinivasarao Arulananda; Sudha, Arya Jayadev; Yasuda, Makoto; Baba, Akio; Tetrahedron; vol. 69; 32; (2013); p. 6598 – 6611;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 37746-78-4

The compound of formula 7-4 (3.0 g, 8.7 mmol, 1 eq) was dissolved in acetonitrile,Ethyl bromocrotonate (1.86 g, 9.6 mmol, 1.1 eq) and potassium carbonate (2.42 g, 17.5 mmol, 2 eq) were added. After the addition, the temperature was raised to 85 C. and the reaction was continued overnight.After the completion of the reaction by thin layer chromatography, the mixture was filtered and spin-dried. Ethyl acetate and water were dissolved and diluted. The layers were separated, and the aqueous phase was extracted with ethyl acetate. The organic phase was combined.After washing with saturated saline, it was dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain 3.94 g of a brown oil (compound of formula 7-5) in 98% yield.

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Yangfan Pharmaceutical Technology Co., Ltd.; Chen Youxi; Gao Fei; He Lidong; (80 pag.)CN104109143; (2018); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 37746-78-4 name is (E)-Ethyl 4-bromobut-2-enoate, 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. 37746-78-4

General procedure: To a 50-mL round-bottomed flask were added ethyl pyrazole-5-carboxylate 1 (1.00 mmol), ethyl 4-bromobut-2-enoate 2 (2.00 mmol), potassium carbonate (0.28 g, 2.05 mmol) and C2H5OH (20 mL). The mixture was refluxed for 8 h. And then they were poured into water (100 mL) and extracted with CH2Cl2 (3 ¡Á 30 mL). The combined extracts were washed with water, dried over anhydrous Na2SO4 and filtered, and the solvent was removed by rotary evaporation. The crude products were purified by column chromatography to afford compounds 3a-f in 42-60%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (E)-Ethyl 4-bromobut-2-enoate, and friends who are interested can also refer to it.

Reference:
Article; Yan, Peiling; Duan, Guiyun; Ji, Ruixue; Ge, Yanqing; Tetrahedron Letters; vol. 59; 25; (2018); p. 2426 – 2429;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics