Category: 25542-62-5

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. 25542-62-5, name is Ethyl 6-bromohexanoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Anhydrous LiCl (1.14 g, 26.89 mmol) was dried in a reaction tube at 160 C. for 20 min under high vacuum. Zn powder (1.75 g, 26.89 mmol) was added under argon and the mixture was dried again at 160 C. under high vacuum. The reaction tube was evacuated and filled with argon three times. THF (15 mL) was added and the Zn was activated with 1,2-dibromoethane (0.06 mL, 0.67 mmol) and TMSCl (0.017 mL, 0.13 mmol). Ethyl 6-bromohexanoate (3 g, 13.45 mmol) was added and the reaction mixture was stirred at 55 C. overnight. The solution 1 was carefully separated from excess zinc using a dry syringe. 3-bromobenzaldehyde (1.5 g, 8.1 mmol) was dissolved in THF (5 mL). Pd2(dba)3 (0.074 g, 0.08 mmol) and t-Bu3P (0.162 mL, 0.162 mmol, 1M) was added. The solution of the organozincate compound 1 in THF (1.5 equivalent) was added to the reaction. The mixture was stirred for 30 min at it (room temperature) and then quenched with NH4Cl (aq. sat.: aqueous saturated solution). The mixture was extracted with Et2O. The combined organic phase was dried, concentrated and purified by flash chromatography to give the ester 2 (1.95 g, 7.858 mmol, 97%). 1H NMR (250 MHz, CDCl3): delta=9.96 (s, 1H), 7.60-7.72 (m, 2H), 7.37-7.46 (m, 2H), 4.08 (q, J=7.1 Hz, 2H), 2.66 (t, J=7.5 Hz, 2H), 2.26 (t, J=7.4 Hz, 2H), 1.56-1.71 (m, 4H), 1.26-1.42 (m, 2H), 1.21 (t, J=7.1 Hz, 3H); HRMS (EI+): [M]+ calculated for C15H20O3, 248.1412. found 248.1413.

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; UNIVERSITY DE SANTIAGO DE COMPOSTELA; UNIVERSIDADE DA CORUNA; SERVIZO GALEGO DE SAUDE (SERGAS); PEREZ FERNANDEZ, Roman; SEOANE RUZO, Samuel; MOURINO MOSQUERA, Antonio; MAESTRO SAAVEDRA, Miguel; CASTELAO FERNANDEZ, Jose Esteban; GOGOI, Pranjal; (41 pag.)US2016/297731; (2016); A1;,
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Reference of 25542-62-5, 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. 25542-62-5 name is Ethyl 6-bromohexanoate, 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.

Reactions were carried out in a Biotage Initiator 60 Microwave Reactor, employing the 20mL process-scale reactor vials. Thirteen (13) identical reactions at the 10 mmol scale were setup in parallel and processed in serial, as follows: All three (3) reagents and reaction solvent were added to the MW vial in the following sequence; (1) ethyl-bromo-hexanoate (1.77 mL), (2) salicylaldehyde (1.05 mL), (3) cesium carbonate (CS2CO3) (3.91 g) and (4) reaction solvent DMA (17.18 mL). Care was taken to dispense the N-N-dimethylacetamide (DMA) solvent in such a manner so as to wash down the vial walls of reactant or solid base. To each vial was added a magnetic stir bar and fitted with a crimp seal cap and adapter collar. The reactions were than process in the MW Reactor for 10 minutes (at temperature) at 140 C with mixing. Following standard ramp up, fixed hold time at temperature and cool down, samples were kept sealed at ambient temperature until the entire lot was processed. The reaction mixtures were combined and transferred to a 2L separatory funnel. Vial contents were washed with ethyl acetate (EtOAc), and a total EtOAc layer of about 800 mL was added. To this was added 800 mL of 1.0 N NaOH solution, and the two layers were vigorously shaken and mixed and then separated. The NaOH aqueous layer was back-extracted 3 x 250 mL with EtOAc, and all the organic layers were combined (about 750 mL) and washed with 800 mL of 1.0 M citric acid solution. The citric acid layer was again back extracted with EtOAc (3 x 250 mL), and the organic layers were again combined (about 1.5 L) and washed (3 x 500 mL) with brine (saturated NaCl), dried over sodium sulfate (Na2SO t) and concentrated to dryness in vacuo. Silica gel TLC (3: 1 Hexanes-EtOAc) Rf = 0.34 (product), Rf = 0.45, 0.25 (trace impurities). Theoretical yield = 13 x 2.64 g or 34.32 g (130 mmol). Isolation and Observed yield = 33.30 g, (33.30 g/34.32 g x 100) = 97%. NMR (, 13C, COSY) and LCMS (ESI+/-) conform to structure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 6-bromohexanoate, and friends who are interested can also refer to it.

Reference:
Patent; SALK INSTITUTE FOR BIOLOGICAL STUDIES; MITOKYNE, INC.; EVANS, Ronald; BAIGA, Thomas, J.; BOCK, Mark, G.; DOWNES, Michael; EMBLER, Emi, Kanakubo; FAN, Weiwei; KEANA, John, F.W.; KLUGE, Arthur, F.; NOEL, Joseph, P.; PATANE, Mike, A.; WO2014/165827; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 25542-62-5, 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. 25542-62-5 name is Ethyl 6-bromohexanoate, 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 2. Synthesis of ethyl 6-(6-fluor-2,2-dimethyl-4-oxo-l ,2,3,4-tetrahydrocarbazol-9-yl) hexanoate [Foumula 1-3]6-fluoro-2,2-dimethyl-2,3-dihydro-lH-carbazol-4(9H)-on [formula 1-2] (0.1 g, 0.43 mmol) was dissolved in DMF (20 mL), and NaH(0.015 g, 0.645 mmol) was added and stirred for 10 minutes. Then, ethyl 6-bromohexanoate (0.096 g, 0.43 mmol) was added and stirred at 60C for 12 hours. After the completion of the reaction, DMF was distilled out under reduced pressure, the reaction mixture was extracted with ethyl acetate and saturated NaHC03 aqueous solution, the organic layer was washed with brine, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. Residue was purified by column chromatography (Si02; hexane/ethylacetate, 3/1 ) to yield the title compound (0.18 g, 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 6-bromohexanoate, and friends who are interested can also refer to it.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; KIM, Yuntae; LEE, Changsik; YANG, Hyun-mo; CHOI, Hojin; MIN, Jaeki; KIM, Soyoung; KIM, Dal-Hyun; HA, Nina; KIM, Jung-Min; LIM, Hyojin; KO, Eunhee; WO2013/62344; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

25542-62-5, 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. 25542-62-5, name is Ethyl 6-bromohexanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedeure: In a 250-mL round-bottom flask, 4-hydroxybenzaldehyde (5g, 41 mmol, 1eq.) and K2CO3( 14g,101 mmol, 2.5eq) were dissolved in anhydrous DMF (25 mL). Ethyl 6-bromohexanoate (13.7g, 61 mmol, 1.5 eq.) was slowly added to the solution under nitrogen atmosphere and refluxed for 2-4 h. Reaction was monitored by TLC. The solution was filtered over Celite 535, diluted with ethyl acetate (150 mL), and washed with brine (100 mLx2). The organic phase was dried over MgSO4, filtered, and concentrated. The crude product, a colorless oil (10.66 g, 40 mmol, 99%), was used without further purification.

The synthetic route of Ethyl 6-bromohexanoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mitachi, Katsuhiko; Salinas, Yandira G.; Connelly, Michele; Jensen, Nicholas; Ling, Taotao; Rivas, Fatima; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4536 – 4539;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

25542-62-5, A common compound: 25542-62-5, name is Ethyl 6-bromohexanoate, 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.

Example 9 Synthesis of 3-[3-(5-carboxypentyl)-5-iodo-2,3-dimethyl-3H-1-indoliumyl]-1-propanesulfonate (2) A mixture of 13.4 g (0.12 mol) of potassium tert-butoxide and 100 g of tert-butanol was stirred and heated until the tert-butoxide totally dissolved. The solution was cooled to about 50 C. and 17 g (0.12 mmol) of ethyl 2-methylacetoacetate was added dropwise. Ethyl-6-bromohexanoate (30 g, 0.13 mmol) was then added dropwise and the reaction mixture was stirred and refluxed for 5 hours. The mixture was filtered and the solvent was removed under reduced pressure. The residue was partitioned between 1M HCl and chloroform. The organic layer was dried over magnesium sulfate and purified on silica gel using 1:10 ethyl acetate/hexane as the eluent to yield 25 g (75%) of diethyl 2-acetyl-2-methyloctanedioate (3) as yellow liquid.

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, Ethyl 6-bromohexanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NANOQUANTUM SCIENCES, INC.; Jones, Gary W.; Tatarets, Anatoliy L.; Patsenker, Leonid D.; US2013/231604; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 25542-62-5, name is Ethyl 6-bromohexanoate, 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 25542-62-5. 25542-62-5

General Procedure 1: Preparation of Azides from Aliphatic BromidesAt RT, excess sodium azide (about 4-6 eq.) is added to a solution of the appropriate bromide in DMF (about 0.2 to 1 mol/l). The suspension is stirred vigorously at 50-80 C. for 2-18 h. After cooling to RT, the reaction mixture is diluted (for example with ethyl acetate or dichloromethane) and washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. After careful concentration under reduced pressure, the crude product may, if required, be purified by chromatography on silica gel (typical mobile phase mixture, for example, cyclohexane/ethyl acetate 100:1 to 10:1).

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 Ethyl 6-bromohexanoate.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/28971; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics