Category: 106614-28-2

Synthetic Route of 106614-28-2,Some common heterocyclic compound, 106614-28-2, name is Methyl 2,4-difluorobenzoate, molecular formula is C8H6F2O2, 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.

Methyl 2,4-difluorobenzoate (1.00 g; 5.81 mmol), 4-fluorophenol (0.72 g; 6.39 mmol) and potassium carbonate (1.61 g; 11.62 mmol) in DMF (20 mL) are stirred at 90C for 4 hours. The reaction mixture is diluted with water and extracted three times with DCM. The combined organic layers are dried over MgSC , filtered and concentrated under reduced pressure. The residue is purified by RP-HPLC (ACN/water + TFA). Yield: 0.45 g (29%) ESI-MS: m/z = 265 [M+H]+ Rt(HPLC): 1.15 min (method 1)

The synthetic route of 106614-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela Kay; BOUYSSOU, Thierry; GOTTSCHLING, Dirk; HEINE, Niklas; NETHERTON, Matthew Russell; (119 pag.)WO2019/161010; (2019); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 106614-28-2, name is Methyl 2,4-difluorobenzoate, 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 106614-28-2, SDS of cas: 106614-28-2

Intermediate 28: Methyl 2-fluoro-4-(piperazin-1-yl)-benzoate Dimethyl sulfoxide (1.0 ml) was added to 544 mg of piperazine to prepare a suspension, and 368 mg of methyl 2,4-difluorobenzoate was added to the suspension. The mixture was stirred at 80 C. for 1 hr and was then cooled to room temperature. The reaction solution was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (development system: methylene chloride-methanol-concentrated aqueous ammonia=900:100:1) to prepare 274 mg of the title compound. Physicochemical Properties of Intermediate 28

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Reference:
Patent; Meiji Seika Kaisha, Ltd.; US6451800; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 106614-28-2, The chemical industry reduces the impact on the environment during synthesis 106614-28-2, name is Methyl 2,4-difluorobenzoate, I believe this compound will play a more active role in future production and life.

To a mixture of methyl 2,4-difluoro benzoate (1.0 g) in 1,4-dioxane (20 mL), 5-hydroxypyrrolo[2,3-b]pyridine (779 mg) and K3P04 (1.47 g) were added at 34C and heated to90C. The reaction mixture is stirred at the same temperature for 23 hours. K3P04 (396mg) was added at 90C to the reaction mixture and stirred for another 24 hours at thesame temperature. Cooled the reaction mixture to 32C and filtered on a celite bed.Washed the celite bed with ethyl acetate (20 mL) and evaporated the solvent in the filtrateto obtain crude product. The crude product was purified by column chromatography using60-120 silica gel mesh and 10-50% ethyl acetate- hexane as eluent to obtain the titlecompound as white solid. Yield: 588 mg; Purity by HPLC: 98.73%

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 2,4-difluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DR. REDDY?S LABORATORIES LIMITED; PEDDIREDDY, Subba Reddy; KOTTUR, Mohan Kumar; JURUPULA, Ramprasad; BAIG, Mohammed Azeezulla; CHAKKA, Ramesh; THIPPARABOINA, Rajesh; PEDDY, Vishweshwar; RAO, Pallavi; ORUGANTI, Srinivas; DAHANUKAR, Vilas Hareshwar; (88 pag.)WO2017/212431; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

106614-28-2, 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 106614-28-2 as follows.

To a 50 mL round bottom flask purged with and maintained 1..mder an inertatmosphere of nitrogen v.¡¤as added (1 S,4S,5R)-5-[[5-cyclopropyl-3-(2,6-dichloropheny l)- L2-oxazol-4-yl]rnethoxy]-2-azabicyclo[2.2.1]heptane hydroiodide salt l2dd (250 rng, 0.49 mmol, 1.00 equiv.), methyl2,4-dit1uorobenzoate (225 mg, 1.31 mmol, 2.67 equiv.), CsF (298rng, 196 mmol, 4.00 equiv.), and 1-Ethyl-3-methylimidazoliurn dimethyl phosphate (3 mL)The resulting mixture was heated at 90C overnight After cooling to room temperature, themixtme wa;;; diluted with 20 mL off-hO and extracted with ethyl acetate (30 mL x 2). The5 cornbined organic extracts were washed with brine (30 mL x 3), dried over anhydrous sodiumsulfate and concentrated under vacuum. The residue was purified by silica gel columnchromatography eluting ~ith ethyl acetate/petroleum ether (I: 3). Removal of solventsafforded methy 14-[(1 S,4S,5R)-5-[[5-cydopropyl-3-(2,6-dichloropheny 1)-1,2-oxazol-4-y l]methoxy]-2-azabicyclo[2.2.l ]hepi:m-2-yl]-2-fluorobenzoate T-177 (158 6 mg, 50%) as an10 off-white solid. 1H-NMR (300 MHz, CDCb): 8 7.77 (t, J = 8.7 Hz, lH), 7.49-7.29 (m 3H),6.22 (dd, J ” 8.8, 2.4 Hz, 1H), 6.10 (dd, J ” 14.3, 2.3 Hz, 1H), 4.28 (s, 2H), 4.04 (s, lH), 3.87(s, 3H), 3.54- 3.44 (m, H-T), 3.35 (dd, J ‘” 9.3, 4.0 Hz, 1H), 2.63- 2.49 (m, 2H), 2.12 (ddt, J= 12.9, 9.6, 4.8 Hz, lH), l 85 (ddd, J = 13.3, 6.8, 2.4 Hz, IH), 1.71 – 1..54 (m, 2H), 1.41-1.22 (m, 3H), 1.27–1.03 (m, 2H): MS (ES, mlz): [M+1] = 531.05.

According to the analysis of related databases, Methyl 2,4-difluorobenzoate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 106614-28-2, name is Methyl 2,4-difluorobenzoate, 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. 106614-28-2

To a three-necked flask was added 100 g of 5-hydroxy-7-azaindole (746 mmol), 141 g of methyl 2,4-difluorobenzoate(821 mmol), 237 g of potassium phosphate (1.12 mol) and 500 mL of diethylene glycol dimethyl Ether, 110 C for 24 h (HPLC to monitor 5-hydroxy-7-azaindole).The reaction solution was concentrated to dryness, and 2L of ethyl acetate and 2 L of water were added. The organic phase was separated,dried over anhydrous sodium sulfate, and concentrated to dry crude.The crude product was heated to reflux with 1260 mL of ethyl acetate. The mixture was slowly added dropwise to a solution of 1260 mL ofpetroleum ether. After 1 h of dropping, the mixture was stirred for 1 h, slowly cooled to 25 C, filtered and dried to give163g of pale white solidRate of 76.5%.HPLC purity 98%.

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, 106614-28-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hangzhou Keyao Pharmaceutical Technology Co., Ltd.; Zhou Junming; (10 pag.)CN107089981; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 106614-28-2, name is Methyl 2,4-difluorobenzoate, 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. 106614-28-2

To a 8 mL sealed tube was added (1S,4S,5R)-5-[[l-(2-chloro-6-methylphenyl)-4- cyclopropyl-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptane 8g (100 mg, 0.28 mmol, 1.00 equiv.), methyl 2,4-difluorobenzoate (72 mg, 0.42 mmol, 1.50 equiv.), CsF (0.134 g, 3.00 equiv.), and l-Ethyl-3-methylimidazolium dimethyl phosphate (1 mL). The resulting mixture was heated at 90 C overnight. After cooling to room temperature, the mixture was diluted with 20 mL of H2O, and extracted with ethyl acetate (100 mL x 2). The combined organic extracts were washed with brine (100 mL x 2), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1 :2) to afford methyl 4-[(1S,4S,5R)-5-[[l-(2-chloro-6-methylphenyl)-4- cyclopropyl-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptan-2-yl]-2-fluorobenzoate 8h (91 mg, 64%) as a red oil.

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 106614-28-2.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics