Category: 653-92-9

Electric Literature of 653-92-9, 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. 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Methyl 2-bromo-4-fluorobenzoate (3 g), EXAMPLE 1B (4.43 g), and K2CO3 (3.56 g) were stirred in DMSO (35 mL) at 125 C. for 24 hours. The mixture was cooled, taken up in ethyl acetate (500 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated. The concentrate was chromatographed on silica gel with 5-25% ethyl acetate/hexanes.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-4-fluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBOTT LABORATORIES; US2010/160322; (2010); A1;,
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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. 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 653-92-9

To a mixture of methyl 2-bromo-4-fluorobenzoate (10.1 g, 43.34 mmol, 1.00 equiv) in THF (100 ml) with Cs2C03 (42 g, 128.91 mmol, 3.00 equiv) and Pd(dppf)CI2 (3.5 g, 4.78 mmol, 0.1 1 equiv) was added Et3B (1 M in tetrahydrofuran) (65 ml, 65 mmol, 1.50 equiv). The reaction mixture was stirred overnight at 80C. Water was added and the mixture was extracted with EA thrice. The combined extracts were washed with water, saturated brine and dried over anhydrous Na2S04, then concentrated and purified by chromatography on silica gel (1 :30 EA/PE) to yield methyl 2-ethyl-4- fluorobenzoate as a yellow oil.

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; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Ester – Wikipedia,
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Related Products of 653-92-9,Some common heterocyclic compound, 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, molecular formula is C8H6BrFO2, 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: Method A: A sealed tube was charged with compound 4a,b (0.93 mmol), 5a-e (0.93 mmol), 5 mol % of Pd(OAc)2, 10 mol % of Xantphos, 2 equiv of Cs2CO3 (1.86 mmol) and 10 mL of 1,4-dioxane. The mixture was degassed and backfilled with argon, the reaction vessel was sealed with a Teflon tap and heated at 100 C for 12 h. The reaction mixture was cooled to rt and concentrated in vacuo. The residue was dissolved in chloroform, washed with 10% citric acid solution, brine solution, dried over anhydrous Na2SO4 and concentrated. The crude compound was purified by flash column chromatography using 3-5% of MeOH/CHCl3 as an eluent to give the title cyclized compound.Method B: To a thick-well borosilicate glass vial (5 mL) was added compound 4a,b (0.23 mmol), compound 5a-e (0.23 mmol), 5 mol % of Pd(OAc)2, 10 mol % of Xantphos, 2 equiv Cs2CO3 (0.46 mmol) and 1,4-dioxane (2 mL). The mixture was degassed and the reaction vial was sealed and placed in the CEM-DISCOVER microwave reactor and irradiated at 100 C for 15 min. After cooled to rt, the product was isolated as above described in method A.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-bromo-4-fluorobenzoate, its application will become more common.

Reference:
Article; Sorra, Kumaraswamy; Mukkanti; Pusuluri, Srinivas; Tetrahedron; vol. 68; 7; (2012); p. 2001 – 2006;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, 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 653-92-9, Product Details of 653-92-9

a) 2-Bromo-4-dimethylamino-benzoic acid methyl ester (7a) To a stirred solution of 5,24 g (22.5 mmol) 2-Bromo-4-fluoro-benzoic acid methyl ester (Rarechemicals) and 60.0 ml dimethylsulphoxid are added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture is stirred for 11h at 70C in an autoclave and is concentrated with high vacuum rotation evaporator at 65C. The residue is diluted with dichloromethane, washed twice with water. The combined water phases are extracted with dichloromethane. The combined dichloromethane phases are washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude is purified by column chromatography and the desired product 7a is obtained in 70 % yield (4,08 g, 15.8 mmol). MS-ESI: 258/560 (M+ +1, 88/83).

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; Bayer Schering Pharma Aktiengesellschaft; EP1897885; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 653-92-9, 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 653-92-9 as follows.

(b) Methyl 2-cyano-4-fluorobenzoate; Methyl 2-bromo-4-fluorobenzoate (1.0 g, 4.29 mmol; see step (a) above) was dissolved in dry DMF (5 mL) and degassed with N2-gas for 5 minutes. CuCN (769 mg, 8.58 mmol) was added and mixture was degassed again before the temperature was raised. The reaction mixture was refluxed for 75 minutes. NaCN (aq, 10%) was added and the mixture was extracted with DCM. The DCM phase was dried through a phase separator and the solvent was removed in vacuo. The crude product was dissolved in toluene and washed once with water. The organic phase was dried over MgS04 and filtered. The solvent was removed in vacuo to give the product (in 94% yield), which was used without further purification. ‘H NMR (500 MHz, CDC13) 5 4.01 (s, 3H), 7.35-7. 42 (m, 1H), 7.52 (dd, 1H), 8.15-8. 23 (m, 1H)

According to the analysis of related databases, 653-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2005/58826; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, 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 653-92-9, 653-92-9

General procedure: Method A:16,17 A two-necked round-bottomed flask equipped with a reflux condenser and a magnetic stir bar was charged with the 2-bromobenzoic acid (20mmol) and freshly distilled methanol (25mL). The solution was heated in a hot water bath, conc. H2SO4 (8mmol) was added slowly and the reaction mixture was refluxed for 24h. After cooling to room temperature around half of the amount of the solvent was removed in vacuo and the residue was partitioned between water (50mL) and diethyl ether (70mL). The organic layer was separated and washed with saturated NaHCO3 (2¡Á50mL), water (50mL) and brine (50mL), dried over anhydrous MgSO4 and the volatiles were removed under reduced pressure. The crude product thus obtained was purified by flash chromatography on silica gel to afford the alkyl-2-halobenzoate. (0023) In a two-necked round-bottomed flask equipped with a reflux condenser and a magnetic stir bar the alkyl 2-halobenzoate (22.5mmol) was dissolved in freshly distilled dry THF (30mL) under argon. The solution was cooled to 0C using an ice bath and NaH (60% in mineral oil, 15mmol) was added portionwise. After stirring for 15min a solution of the alkyl acetate (15mmol) in dry THF (30mL) was added dropwise to the reaction mixture at 0C. The mixture was warmed up, stirred at room temperature for 2h and heated under reflux for 24h. After cooling to room temperature around half of the amount of the solvent was removed in vacuo and the reaction mixture was diluted with toluene (50mL). The resulting mixture was washed with 2N HCl (50mL), saturated NH4Cl (50mL), dried over anhydrous MgSO4 and the volatiles were removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford the alkyl 3-(2?-halophenyl)-3-oxo-propanoate 1.

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, Methyl 2-bromo-4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Weischedel, Heike; Sudheendran, Kavitha; Mikhael, Alevtina; Conrad, Juergen; Frey, Wolfgang; Beifuss, Uwe; Tetrahedron; vol. 72; 24; (2016); p. 3454 – 3467;,
Ester – Wikipedia,
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653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, 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. 653-92-9

Example 9A methyl 4-fluoro-2-phenoxybenzoate Methyl 2-bromo-4-fluorobenzoate (1 g), phenol (0.565 g), cesium carbonate (1.96 g), copper(I) triflate toluene complex (0.087 g), and ethyl acetate (0.034 mL) in toluene (12 mL) was stirred at 110 C. for 24 hours. The reaction was cooled and chromatographed on silica gel with 5% ethyl acetate/hexanes.

Statistics shows that 653-92-9 is playing an increasingly important role. we look forward to future research findings about Methyl 2-bromo-4-fluorobenzoate.

Reference:
Patent; ABBOTT LABORATORIES; US2010/184750; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, 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 653-92-9, 653-92-9

General procedure: A sealed tube of 25 mL equipped with a magnetic stir bar was charged with alkynes (0.20 mmol), 2-bromobenzoic esters (0.22 mmol), CuI (0.02 mmol, 10 mol%), NaOH (0.4 mmol, 2 equiv) and CH3CN (1.0 mL). The reaction mixture was stirred at 100 C for 24 h. The reaction was monitored by GC or GC-MS. After completion of the reaction, the reaction mixture was cooled to room temperature, then washed with saturated NH4Cl aqueous solution (5.0 mL), and extracted with CHCl3 (3 * 5.0 mL). The combined organic phases were dried over Na2SO4 (anhydrous), concentrated in vacuum. The crude product was purified by flash column chromatography (eluent: ethyl acetate/petroleum ether = 1/20-1/10) on silica gel to afford the desired product.

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, Methyl 2-bromo-4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sun, Mengli; Su, Lebin; Dong, Jianyu; Liu, Long; Zhou, Yongbo; Yin, Shuang-Feng; Tetrahedron Letters; vol. 58; 25; (2017); p. 2433 – 2437;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, molecular formula is C8H6BrFO2, 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. 653-92-9

To a solution of methyl 2-bromo-4-fluoro-benzoate (90 g, 386.21 mmol, 1 eq) in dimethylsulfoxide (500 mL) was added tert-butyl piperazine-1-carboxylate (111.82 g, 502.07 mmol, 1.3 eq, hydrochloric salt) and N,N-diisopropylethylamine (199.66 g, 1.54 mol, 269 mL, 4 eq). The mixture was heated to 130 C and stirred at 130 C for 36 hours. The mixture was poured into 1.0 L water, and extracted with ethyl acetate (500 mL x 2). The organic layer was washed with water (1000 mL), 0.5 M hydrochloric acid (500 mL), saturated brine (500 mL) and then dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was triturated with (petroleum ether : ethyl acetate =5:1, 300 mL), the solid was filtered and dried in vacuum. tert-butyl 4-(3-bromo-4-methoxycarbonyl-phenyl)piperazine-1-carboxylate (93 g, 232.92 mmol, 60% yield) was obtained as an off-white solid. LC/MS (ESI) m/z: 422.1 [M+23] +; 1H-NMR (400MHz, DMSO-d6) d 7.73 (d, J=8.8 Hz, 1H), 7.18 (d, J=2.4 Hz, 1H), 6.98 (dd, J=8.8, 2.4 Hz, 1H), 3.77 (s, 3H), 3.45-3.42 (m, 4H), 3.34-3.31 (m, 4H), 1.42 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 653-92-9, its application will become more common.

Reference:
Patent; ARVINAS OPERATIONS, INC.; YALE UNIVERSITY; CREW, Andrew P.; HORNBERGER, Keith R.; WANG, Jing; CREWS, Craig M.; JAIME-FIGUEROA, Saul; DONG, Hanqing; QIAN, Yimin; ZIMMERMAN, Kurt; (1451 pag.)WO2020/51564; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

653-92-9, 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. 653-92-9 name is Methyl 2-bromo-4-fluorobenzoate, 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.

Into a 250-mL round-bottom flask, was placed a solution of Example 1-i, i.e, 1- [[2-(4-chlorophenyl)-4,4-dimethylcyclohex- i-en-i -ylj methyljpiperazine (15.09 g, 47.32 mmol, 1.00 equiv) in DMA (150 mL), DIEA (12.9 g, 99.81 mmol, 2.00 equiv), methyl 2-bromo-4-fluorobenzoate (11.6 g, 49.78 mmol, 1.00 equiv). The resulting solution was stirred for 12 h at 100 degree. The reaction mixture was cooled to room temperature. The reaction was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3xiOO mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3xiOO mL of brine. The mixture was dried over anhydrous sodium sulfate, then filtered and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0:1-1:5). This resulted in 7 g (crude) of methyl 2-bromo-4-(4-[[2- (4-chlorophenyl)-4,4-dimethylcyclohex- i-en-i -ylj methyljpiperazin- 1 -yl)benzoate as yellow oil. LC-MS: (ES, m/z): M+i=533, 531.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromo-4-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; LOU, Yan; (108 pag.)WO2019/40550; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics