Category: 24398-88-7

24398-88-7, Adding a certain compound to certain chemical reactions, such as: 24398-88-7, name is Ethyl 3-bromobenzoate, belongs to esters-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 24398-88-7.

The N-(3-amino-4-methylphenyl)-3-morpholinobenzamide used as a starting material was prepared as follows: A mixture of ethyl 3-bromobenzoate (1.92 ml), morpholine (1.25 ml), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.336 g), sodium tert-butoxide (1.615 g) and tris(dibenzylideneacetone)dipalladium(0) (0.33 g) and toluene (25 ml) was stirred and heated to 90 C. for 18 hours under argon. The reaction mixture was allowed to cool to ambient temperature and extracted with 1M hydrochloric acid. The aqueous phase was basified with concentrated sodium hydroxide solution and extracted with ethyl acetate. The organic phase was dried over magnesium sulphate, filtered and evaporated to dryness. The residual oil was purified by column chromatography on silica gel using a 47:3 mixture of methylene chloride and methanol as eluent to yield N-(3-morpholinobenzoyl)morpholine (0.45 g).

According to the analysis of related databases, 24398-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astrazeneca AB; US6593333; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

24398-88-7, name is Ethyl 3-bromobenzoate, belongs to esters-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. 24398-88-7

Step 1 : Ethyl 3-(3-methoxypropyl)benzoateTo a THF solution (0.1 M) of allyl methyl ether (1.4 eq.) was added, at 0 0C, 9- borabicyclo[3.3.1]nonane (2.4 eq.) over a period of 30 min. The solution was stirred at 0 0C for 1 h and then warmed slowly to RT over 16 h. To the resulting clear solution was then added sodium methoxide (2.4 eq.), Cl2Pd(dppf)-dichloromethane complex (5% loading) and ethyl 3-bromobenzoate (1 eq.). The now brown suspension was heated to reflux for 16 h. The reaction mixture was cooled to RT, quenched with sat. aq. NH4Cl and extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a brown oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex -^ 4: 1 (v/v) Hex : EtOAc) afforded the title compound as a light yellow oil.

Statistics shows that 24398-88-7 is playing an increasingly important role. we look forward to future research findings about Ethyl 3-bromobenzoate.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2007/9250; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

24398-88-7, Adding some certain compound to certain chemical reactions, such as: 24398-88-7, name is Ethyl 3-bromobenzoate, 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 24398-88-7.

3-bromobenzoicacid ethyl ester 25 (1.5g, 6.6mmol) was dissolved in 15mL of ethanol, then under ice-cooling was slowly added dropwise with hydrazine hydrate (1.3g,26mmol), after the addition was complete, it was stirred at room temperaturefor 15min, then heated under reflux for 10h. After completion of the reaction, ethanol was removed by rotary evaporation, poured into water, extracted with ethyl acetate, the organic phase was dried and concentrated to give the desired product 26 (1.1g, 78%), without purification into the next step.

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 24398-88-7.

Reference:
Patent; Jiangshu Alpha Biopharmaceuticals, Inc.; Jiangnan University; Nanjing Drum Tower Hospital; Feng, Bainian; Yang, Guijun; Tang, Chunlei; Wang, Guping; Jie, Desheng; (36 pag.)CN105481765; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 24398-88-7, name is Ethyl 3-bromobenzoate, 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. 24398-88-7

The zinc reagent 2c was prepared according to TP1 from methyl3-bromo-4-(((trifluoromethyl)sulfonyl)oxy)benzoate (1c,7.26 g, 20 mmol), Zn-powder (3.92 g, 60 mmol) and InCl3(0.33 g, 1.5 mmol). The reaction mixture was stirred in DMPU(20 mL) at 50 C for 2 h. Iodolysis indicated a yield of 70% bimetallic reagent (14 mmol). The solution containing the zinc reagent was separated from the remaining zinc powder and transferred to a new flask containing a solution of ethyl 3-bromobenzoate (3e, 9.16 g, 40 mmol) and PEPPSI-iPr (0.19 g,0.28 mmol) in THF (20 mL). The reaction mixture was stirred at 50 C for 12 h before being quenched with HCl (2 M, 50 mL). Flash column chromatographical purification on silica gel(pentane/diethyl ether = 4:1) afforded 4e as a colorless oil (3.82 g, 8.83 mmol, 63%).

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, 24398-88-7, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Klatt, Thomas; Bluemke, Tobias D.; Ganiek, Maximilian A.; Knochel, Paul; Synthesis; vol. 46; 3; (2014); p. 290 – 294;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 24398-88-7 as follows. 24398-88-7

[00457] To a stirred solution of 1.3 M LHMDS (25 mL, 32.7 mmol) in THF (10 mL) was added EtOAc (1.9 g, 21.8 mmol) at -78 C under inert atmosphere. After being stirred for 15 min, ethyl- 3-bromo benzoate (5 g, 21.8 mmol) was added and stirring was continued for 2 h; progress of the reaction was monitored by TLC. The reaction was quenched with aq. NH4C1 (10 mL) and extracted with EtOAc (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude product. The crude material was purified by silica gel column chromatography eluting with 4% EtOAc/Hexane to afford compound G (4.5 g, 76.9%) as a mixture with its enolic form as a brown oil. 1H NMR (500 MHz, CDCls): delta 8.07 (s, 1H), 7.86 (d, J= 7.5 Hz, 1H), 7.73-7.69 (m, 1H), 7.37 (t, J= 7.0 Hz, 1H), 4.28-4.26 (m, 2H), 3.92 (s, 2H), 1.24 (t, J= 6.2 Hz, 3H). MS (ESI): m/z 298.8 [M-l].

According to the analysis of related databases, 24398-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; COSFORD, Nicholas David, Peter; DHANYA, Raveendra, Panickar; SHEFFLER, Douglas, J.; WO2015/191630; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 24398-88-7, name is Ethyl 3-bromobenzoate, 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. 24398-88-7

General procedure: To an undivided electrochemical cell, fitted with an iron/nickel (64/36) rod as the anode and surroundedby a nickel foam as the cathode, were added DMF (50 mL), tetrabutylammonium bromide (1.2 mmol, 400mg), and 1,2-dibromoethane (2.5 mmol, 215 muL). The mixture was electrolyzed under argon at a constantcurrent intensity of 0.2 A at room temperature for 15 min. The current was then stopped, and the NiBr2bpycomplex (0.4 mmol, 150 mg), 3-amino- or 3-alkoxy/aryloxy-6-chloropyridazine (4 mmol), and aromatic orheteroaromatic halides (8 mmol) were sequentially added. The solution was electrolyzed at 0.2 A at roomtemperature until one of the starting materials was totally consumed. A saturated aqueous solution of EDTAsodium salt (100 mL) was added to the mixture, and the solution was extracted with dichloromethanecontaining 2-5% methanol (3 ¡Á 100 mL). The combined organic layers were dried over MgSO4, filtered,and evaporated under vacuum. The crude product was purified by flash chromatography on silica, elutedwith a gradient of solvents (pentane/acetone). For some polar cross-coupling compounds, a mixture ofacetone/methanol (95/5) was necessary.

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 24398-88-7.

Reference:
Article; Sengmany, Stephane; Sitter, Mathilde; Leonel, Eric; Le Gall, Erwan; Loirand, Gervaise; Martens, Thierry; Dubreuil, Didier; Dilasser, Florian; Rousselle, Morgane; Sauzeau, Vincent; Lebreton, Jacques; Pipelier, Muriel; Le Guevel, Remy; Bioorganic and Medicinal Chemistry Letters; vol. 29; 5; (2019); p. 755 – 760;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

24398-88-7, A common heterocyclic compound, 24398-88-7, name is Ethyl 3-bromobenzoate, molecular formula is C9H9BrO2, 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.

1-(6-(dibutyl(3-(ethoxycarbonyl)phenyl)stannyl)hexyl)-3-ethyl-1H-imidazol-3-ium bromide I’a-14(Br-) A dried 50 mL Schlenk tube was flushed with argon and charged with zinc dust (1.36 g, 20.8 mmol, 5 eq) and cobalt(II) bromide (0.095 g, 0.4190.434 mmol, 0.1 eq). The mixture was activated under vacuum at 150C during 4 h. Acetonitrile (5 mL) was added to the cooled mixture then trifluoroacetic acid (0.15 mL) and 1,2-dibromoethane (0.1 mL) were added and the resulting solution stirred for additional 15 minutes (an increase of temperature was observed). Then ethyl 3-bromobenzoate (1.46 g, 6.36 mmol, 6.3 eq) was introduced to the mixture which was stirred at room temperature for 12 h. The resulting solution of arylzinc reagent was introduced dropwise to the ionic liquid (Va-1) (529 mg, 1.0 mmol, 1 eq) in solution in THF (6 mL). After 18 h of stirring at room temperature, the resulting mixture was filtered through a short pad of silica gel then extracted with CH2Cl2 (3 x 100 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (CH2Cl2 to CH2Cl2/MeOH 90:10) to afford compound I’a-14(Br-) as viscous yellow oil (450 mg, 70 %). 1H NMR (CDCl3): delta 10.17 (s, 1H), 8.14 (bs, 1H), 7.92 (d, J = 7.8 Hz, 1H), 7.62 (d, J = 7.2 Hz, 1H), 7.39 (dd, J = 7.5 Hz, J = 7.5 Hz, 1H), 7.30 (bs, 1H), 7.23 (bs, 1H), 4.48-4.33 (m, 4H), 4.32 (t, 2H, J = 7.2 Hz), 1.89-1.78 (m, 2H), 1.61-1.47 (m, 9H), 1.42-1.24 (m, 11H), 1.13-1.00 (m, 6H), 0.87 (t, J = 7.2 Hz, 6H). 13C NMR 75 MHz (CDCl3) delta (ppm): 166.8, 141.9, 140.6, 136.9, 135.9, 129.4, 128.8, 127.5, 122.0, 121.8, 60.6, 49.8, 45.1, 33.4, 30.0, 28.7, 27.0, 26.3, 25.5, 15.5, 14.4, 13.4, 9.4, 9.3. HRMS (FAB) calcd. for C28H47N2O2Sn 563.2654 [M-Br]+; found 563.2675.

The synthetic route of 24398-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Centre National de la Recherche Scientifique (CNRS); UNIVERSITE DE NANTES; UNIVERSITE D’ANGERS; Universite du Maine; Institut National de la Sante et de la Recherche Medicale (INSERM); Centre Hospitalier Universitaire De Nantes; Legoupy, Stephanie; Faye, Djibril; Gestin, Jean-Francois; Rajerison, Holisoa; Faivre-Chauvet, Alain; Boeda, Fabien; EP2891657; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

24398-88-7, 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 24398-88-7 as follows.

A mixture of 3- bromo-benzoic acid ethyl ester (229 mg, 1 mmol), 4-methylpiperidine ( 120 mg, 1 .2 mmol ), Pd2(dba)3 (25 mg ), BINAP (25 mg), and fBuONa ( 130 mg ) in toluene (6 mL) was heated at 90 C overnight. After the reaction was completed as indicated by TLC, the mixture was filtered and the filtrate was concentrated in vacuo. Ethyl acetate (50 mL) and aq. HC1 ( I , 20 mL) were then added. The aqueous portion was extracted with ethyl acetate (2 x 50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate, and filtered, concentrated, and purified by chromatography to give the title compound (76 mg, 3 1 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 24398-88-7, and friends who are interested can also refer to it.

Reference:
Patent; ARGUSINA INC.; LIAO, Jiayu; HONG, Yufeng; WANG, Yong; VON GELDERN, Thomas W.; ZHANG, Kanyin E.; WO2011/94890; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

24398-88-7, 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. 24398-88-7, name is Ethyl 3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of ethyl-3-bromobenzoate (3.0 g, 13 mmol), [3-(hydroxymethyl)- phenyl]boronic acid (3.0 g, 20 mmol), PdCl2(PPh3)2 (0.46 g, 0.66 mmol), K2CO3 (3.6 g, 26 mmol), methanol (4 mL), and toluene (36 mL) was heated at 80 0C for 18 h under N2 and then allowed to cool to rt. The reaction mixture was filtered through Celite and then poured into a mixture of ethyl acetate and brine. The two layers were separated and the aqueous layer was extracted with ethyl acetate (x 3). The organic extracts were dried (Na2SO4), filtered, concentrated and purified by silica gel chromatography to give ethyl 3′- (hydroxymethyl)biphenyl-3-carboxylate as an orange oil. A solution Of CBr4 (5.8 g, 17 mmol) and CH2Cl2 (20 mL) was added dropwise to a solution of the above alcohol, PPh3 (4.6 g, 18 mmol), and CH2Cl2 (50 mL) at 0 0C under N2. The reaction was allowed to warm to rt, maintained for 2 h, concentrated, and purified by silica gel chromatography to give ethyl 3′- (bromomethyl)biphenyl-3-carboxylate as a clear oil. Ethyl 3′-(bromomethyl)biphenyl-3- carboxylate was used to alkylate l-(2,2-dimethylpropyl)-4-propyl-lH-indol-5-ol following the procedure outlined in example 1. A mixture of the above indole (0.66 g, 1.4 mmol), 1 N LiOH (8 mL), and TEtaF (8 mL) was heated at 40 0C for 2 d and then cooled to 0 C- acetone can used in place of TEtaF if faster reaction rates are desired. The reaction was acidified to pEta = 1 with cone. HCl and extracted with ethyl acetate (x 3). The organic extracts were dried (Na2SO4), filtered, concentrated and purified by silica gel chromatography to give a yellow oil. 1H NMR (CDCl3, 500 MHz) delta 8.39 (s, IH), 8.11 (d, IH), 7.85 (d, IH), 7.76 (s, IH), 7.59- 7.48 (m, 4H), 7.12 (d, IH), 7.05 (d, IH), 6.96 (d, IH), 6.46 (d, IH), 5.16 (s, 2H), 3.84 (s, 2H), 2.95 (t, 2H), 1.76 (m, 2H), 1.01 (t, 3H), 0.99 (s, 9H). MS (ESI): 456 (M+H).

The synthetic route of 24398-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/91496; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics