Category: 6942-39-8

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. 6942-39-8, name is Methyl 2-bromo-5-fluorobenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C8H6BrFO2

A 500 mL round-bottom flask was charged with methyl 2-bromo-5- fluorobenzoate (48 g, 206 mmol), copper cyanide (37 g, 412 mmmol) and DMF (200 mL). The mixture was heated at 110 C overnight and then cooled to room temperature. Ether (1.5 L) and Celite (100 g) were added and the mixture was stirred at room temperature for 30 minutes. The solid was filtered and the filtrate was washed with brine (3 x 200 mL) and then dried over MgS04. The solvent was evaporated under reduced pressure to give the desired product as a colorless solid (31 g, 84%). MS : (ES) m/z calculated for C9H7FN02[M+H]+ 180.1, found 180.1.

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; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean, R.; FAN, Junfa; KALISIAK, Jaroslaw; KRASINSKI, Antoni; LELETI, Manmohan, Reddy; MALI, Venkat; MCMAHON, Jeffrey; SINGH, Rajinder; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; (198 pag.)WO2017/87607; (2017); A1;,
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. 6942-39-8, name is Methyl 2-bromo-5-fluorobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6BrFO2

A 500 mL round-bottom flask was charged with methyl 2-bromo-5- fluorobenzoate (48 g, 206 mmol), copper cyanide (37 g, 412 mmmol) and DMF (200 mL). The mixture was heated at 110 C overnight and then cooled to room temperature. Ether (1.5 L) and Celite (100 g) were added and the mixture was stirred at room temperature for 30 minutes. The solid was filtered and the filtrate was washed with brine (3 x 200 mL) and then dried over MgS04. The solvent was evaporated under reduced pressure to give the desired product as a colorless solid (31 g, 84%). MS : (ES) m/z calculated for C9H7FN02[M+H]+ 180.1, found 180.1.

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; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean, R.; FAN, Junfa; KALISIAK, Jaroslaw; KRASINSKI, Antoni; LELETI, Manmohan, Reddy; MALI, Venkat; MCMAHON, Jeffrey; SINGH, Rajinder; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; (198 pag.)WO2017/87607; (2017); A1;,
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 6942-39-8 as follows. Recommanded Product: Methyl 2-bromo-5-fluorobenzoate

Example 16a) 2-Bromo-5-dimethylamino-benzoic acid methyl ester (16a)To a stirred solution of 5,24 g (22.5 mmol) 2-Bromo-5-fluoro-benzoic acid methyl ester (Rarechemicals) and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 11 h at 7O0C in an autoclave and was concentrated with high vacuum rotation evaporator at 650C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude was purified by column chromatography and the desired product 16a was obtained in 70 % yield (4,08 g, 15.8 mmol).MS-ESI: 258/560 (M+ +1 , 90/81).Elementary analysis: C 46.53% H 4.69% N 5.43%Determined: C 46,59% H 4.72% N 5.41%

According to the analysis of related databases, 6942-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2008/28688; (2008); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 6942-39-8,Some common heterocyclic compound, 6942-39-8, name is Methyl 2-bromo-5-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.

a) 2-Bromo-5-dimethylamino-benzoic acid methyl ester (16a) To a stirred solution of 5,24 g (22.5 mmol) 2-Bromo-5-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 16a is obtained in 70 % yield (4,08 g, 15.8 mmol). MS-ESI: 258/560 (M+ +1, 90/81).

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-5-fluorobenzoate, its application will become more common.

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

Related Products of 6942-39-8, A common heterocyclic compound, 6942-39-8, name is Methyl 2-bromo-5-fluorobenzoate, molecular formula is C8H6BrFO2, 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.

To a solution of methyl 2-bromo-5-fluorobenzoate (18.26 moles) in DMF (total vol. 9.2 L) was charged copper(I) cyanide (1.603 kg) in DMF (5 L) slurry and followed with a DMF flush (4 L). After being degassed, the reaction mixture was heated at 100 C. for 10-16 hours. The reaction mixture was monitored by HPLC (conversion was >98%). After being cooled to 50 C.-60 C., ethyl acetate (20 L) was added, and then 10% NH4OH-20% NH4Cl (22 L). The mixture was then transferred to a 100 L nalgene extractor. The 72 L round bottom flask was washed with 15 L of EtOAc and 15 L of water and transferred to the 100 L extractor. After phase cut, the aqueous layer was back-extracted with EtOAc (17 L) one time. The combined organic layers were washed with 10% NH4OH/20% NH4Cl:water (1:1, 3*10 L), 16% brine (8 L), concentrated, and solvent switched to MeOH (total vol. 22 L, KF=152.6 mug/mL). The resulting solution was used for next step. HPLC conditions: column: Zorbax, Rx C8 250*4.6 mm; temperature: 30 C.; detection at 210 nm; mobile phase: 0.1% aq H3PO4 (A)/MeCN (B); gradient: 90:10 (A)/(B) to 10:90 over 15 min, 10:90 hold for 5 min, 10:90 to 90:10 (A)/(B) over 10 seconds; flow rate: 1 mL/min; retention time for the desired monoester: 11.7 min. Evaporation of a sample to dryness gave a light yellow solid: 1H NMR (CDCl3) delta: 7.86-7.80 (m, 2H), 7.37 (td, J=8.5, 2.6 H, 1H), 4.02 (s, 3H); 13C NMR (100 MHz, CDCl3) delta: 164.3 (d, J=260 Hz), 163.3, 137.1 (d, J=10.0 Hz), 135.2 (d, J=10.0 HZ), 120.2 (d, J=30.0 Hz), 118.8 (d, J=20.0 Hz), 116.6, 109.0, 53.1.

The synthetic route of 6942-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lee, Jaemoon; Zhong, Yong-Li; US2004/220273; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 6942-39-8, 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. 6942-39-8 name is Methyl 2-bromo-5-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.

b)4′-Chloro-4-fluoro-3′-[[(tricyclo[3.3.1.13’7]dec-l-ylmethyl)amino]carbonyl]-[l,l’-biphenyI]-2-carboxylic acid, methyl ester[4-Chloro-3-[[(tricyclo[3.3.1.13>7]dec-l-ylmethyl)amino]carbonyl]phenyl]-boronic acid(Example 2 (a)) (200 mg), 2-bromo-5-fluoro-benzoic acid, methyl ester (Example 51 (a))(170 mg), tetrahydrofuran (2 mL), a solution of potassium carbonate (166 mg) in water (1mL) and fe(triphenylphosphine)palladium(II) chloride (20 mg) were placed in a 10 mLmicrowave vial. The mixture was heated to 70 C for 1 hour in a microwave thenevaporated. The residue was partitioned between dichloromethane (20 mL) and water (20mL). The layers were separated and the aqueous was extracted with dichloromethane(2×20 mL). The combined organics were dried (MgSCU,), filtered and evaporated.Purification by chromatography (SiOa, 1:4 ethyl acetate :isohexane as eluant) gave the sub- title compound as an oil (79 mg).MS: APCI(+ve) 456/458 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromo-5-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2006/25783; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics