Category: 58656-98-7

Application of 58656-98-7, These common heterocyclic compound, 58656-98-7, name is tert-Butyl 4-fluorobenzoate, 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.

tert-butyl 4-(4-hydroxy-4-phenylpiperidin-1-yl)benzoate A solution of 4-hydroxy-4-phenyl piperidine (221 mg, 1.25 mmol) in DMSO (1 mL) was treated with tert-butyl-4-fluorobenzoate (196 mg, 1.00 mmol) and powdered potassium carbonate (173 mg, 1.25 mmol), stirred vigorously at 125 C. for 16 hours, cooled to room temperature, diluted with diethyl ether, washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (DCI(+)) m/e 354 (M+H)+.

Statistics shows that tert-Butyl 4-fluorobenzoate is playing an increasingly important role. we look forward to future research findings about 58656-98-7.

Reference:
Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/55631; (2002); A1;; ; Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/86887; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 58656-98-7, name is tert-Butyl 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 58656-98-7, Application In Synthesis of tert-Butyl 4-fluorobenzoate

Example 57A 4-(4-trans-aminocyclohexyloxy)-benzoic acid tert-butyl ester To a stirred solution of trans-4-aminocyclohexanol (345 mg, 3 mmol) in DMF (9 mL) at 0 C. was added 60% NaH in mineral oil (360 mg, 9 mmol). The reaction mixture was stirred at 0 C. for 1/2 hour and then tert-butyl 4-fluorobenzoate (706 mg, 3.6 mmol) was added. It was heated to 60 C. for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) m/z 292 (M+H)+.

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, tert-Butyl 4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2004/259843; (2004); A1;; ; Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2005/215784; (2005); 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 58656-98-7 as follows. COA of Formula: C11H13FO2

To the solution of tert-butyl 4-fluorobenzoate (500 mg, 2.55 mmol) and 3-hydroxybenzonitrile (306 mg, 2.55 mmol) in N,N-dimethylformamide (80 mL) was added potassium carbonate (528 mg, 3.8 mmol), the mixture was stirred at 130 C. for 1 hour under microwave. Then evaporated the solvent purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=10:1) to give tert-butyl-4-(3-cyanophenoxy)benzoate (185 mg, 57%), as oil, 1H-NMR (300 MHz, CD3OD) delta 8.00 (m, 2H), 7.56 (m, 2H), 7.43 (m, 2H), 7.05 (m, 2H), 1.59 (s, 9H).

According to the analysis of related databases, 58656-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Constellation Pharmaceuticals, Inc.; Albrecht, Brian K.; Audia, James Edmund; Cook, Andrew S.; Gagnon, Alexandre; Harmange, Jean-Christophe; Nasveschuk, Christopher G.; US9206128; (2015); B2;,
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Synthetic Route of 58656-98-7, A common heterocyclic compound, 58656-98-7, name is tert-Butyl 4-fluorobenzoate, molecular formula is C11H13FO2, 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.

816 g of the intermediate 2 was dissolved in 2500 g of o-dichlorobenzene, 900 g of aluminum trichloride was added, andthe o-dichlorobenzene solution of the intermediate 3 of the previous step was added dropwise to the reaction systemat 10-15 C. After the completion of the dropwise addition, thereaction was carried out at 10-15 C for about 3 hours.After the completion of the reaction, 2500 g of a 5.0% aqueous hydrochloric acid solution was added to the system, and the mixture was stirred for 10 minutes, allowed to stand for separation, and the organic phase was retained, and thesolvent was distilled off under reduced pressure at 100-120 C. O-dichlorobenzene was added to 2000 ethanol, heated to 75 C to dissolve, cooled to 0-5 C forcrystallization, and the filter cake was dried at 60 C to obtain 1248 g of intermediate 4.

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; Jiangsu Baozhongbaoda Pharmaceutical Co., Ltd.; Chen Rong; Zhao Haihua; Wang Lin; (8 pag.)CN109535081; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 58656-98-7, These common heterocyclic compound, 58656-98-7, name is tert-Butyl 4-fluorobenzoate, 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.

N,N-Dimethyl-3-oxo-1,2-dihydroindazole-5-carboxamide (900 mg; 4.39 mmol; 1.00 eq.), 1-methyl-2-pyrrolidinone (5.00 mL), cesium carbonate (4.29 g; 13.16 mmol; 3.00 eq.) andtert-butyl 4-fluoro-benzoate (2.58 g; 13.2 mmol; 3.00 eq.) were stirred at 110 C for4 hours. The reaction mixture was cooled, diluted with 50 mL of ethyl acetate. The organic layer was washed with brine (20 mL), water ( 20 mL), dried over MgSO4and concentrated.tert-Butyl 4-(5-(dimethylcarbamoyl)-3-oxo-2,3-dihydro-1H-indazol-1-yl)benzoate is isolated without further purification as a beige solid (900 mg; 53.8%)1H NMR (DMSO-d6) delta: 1.58 (s, 9H), 3.01 (s, 6H), 7.58 (dd,J =8.8, 1.7 Hz, 1H), 7.90 – 7.84 (m, 3H), 7.95 (d,J =8.8 Hz, 1H), 8.08 – 8.03 (m, 2H), 11.77 (s, 1H).MS-ESIm/z382 [MH+].

Statistics shows that tert-Butyl 4-fluorobenzoate is playing an increasingly important role. we look forward to future research findings about 58656-98-7.

Reference:
Article; Ouvry, Gilles; Bouix-Peter, Claire; Ciesielski, Fabrice; Chantalat, Laurent; Christin, Olivier; Comino, Catherine; Duvert, Denis; Feret, Christophe; Harris, Craig S.; Lamy, Laurent; Luzy, Anne-Pascale; Musicki, Branislav; Orfila, Danielle; Pascau, Jonathan; Parnet, Veronique; Perrin, Agnes; Pierre, Romain; Polge, Gaelle; Raffin, Catherine; Rival, Yves; Taquet, Nathalie; Thoreau, Etienne; Hennequin, Laurent F.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5802 – 5808;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 58656-98-7, These common heterocyclic compound, 58656-98-7, name is tert-Butyl 4-fluorobenzoate, 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.

tert-butyl 4-(4-hydroxy-4-phenylpiperidin-1-yl)benzoate A solution of 4-hydroxy-4-phenyl piperidine (221 mg, 1.25 mmol) in DMSO (1 mL) was treated with tert-butyl-4-fluorobenzoate (196 mg, 1.00 mmol) and powdered potassium carbonate (173 mg, 1.25 mmol), stirred vigorously at 125 C. for 16 hours, cooled to room temperature, diluted with diethyl ether, washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (DCI(+)) m/e 354 (M+H)+.

Statistics shows that tert-Butyl 4-fluorobenzoate is playing an increasingly important role. we look forward to future research findings about 58656-98-7.

Reference:
Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/55631; (2002); A1;; ; Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/86887; (2002); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 58656-98-7, 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 58656-98-7 as follows.

5. Synthesis of tert-butyl 4-[6-(2-hydroxyethyl)-2-azaspiro[3.3]heptan-2-yl]benzoate To a solution of tert-butyl 4-fluorobenzoate (10.25 g, 52.24 mmol, 5.012 equiv) in DMSO (50 mL) in a 250-mL round-bottom flask was added DIEA (14 mL, 84.71 mmol, 8.128 equiv). The mixture was stirred for 5 minutes, then 2-[2-azaspiro[3.3]heptan-6-yl]ethan-1-ol; trifluoroacetic acid (2.66 g, 10.42 mmol, 1 equiv) was added. The resulting solution was stirred for 16 hours at 130 C. After cooling to room temperature, the reaction was then quenched by addition of water (100 mL*1). The resulting solution was extracted with ethyl acetate (100 mL*3). The combined organic layers were washed with water (50 mL*2) and brine (50 mL*1). The organic layer was dried over anhydrous sodium sulfate. The crude was subjected to a silica gel column with ethyl acetate/petroleum ether (1:2). This resulted in 311.5 mg (9.42%) of tert-butyl 4-[6-(2-hydroxyethyl)-2-azaspiro[3.3]heptan-2-yl]benzoate as a light yellow solid. LC-MS (ES+): m/z 318.2 [MH+], tR=1.314 min, (2.0 minute run).

According to the analysis of related databases, 58656-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Hornberger, Keith R.; Snyder, Lawrence B.; Zimmermann, Kurt; Wang, Jing; Berlin, Michael; Crews, Craig M.; Dong, Hanqing; (605 pag.)US2018/99940; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 58656-98-7, 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. 58656-98-7, name is tert-Butyl 4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation of 4-[4-(2-Aminoethyl phenoxy]benzoic acid, tert-butyl ester Tyramine (700 mg, 5.1 mmol) was added to a magnetically stirred suspension of potassium hydride (35 wt. percent dispersion in oil; 876 mg, 7.64 mmol) in DMF (20 mL) at 25 C. After effervescence stopped, tert-butyl 4-fluorobenzoate (1.0 g, 5.1 mmol) was added. After stirring at 25 C. for 64 hours, the reaction was warmed to 60 C. After 48 h, the reaction was poured into brine and extracted with hexanes (3*25 mL) and ethyl acetate (2*25 mL). Organic layers washed separately with aqueous 2 N NaOH, dried (Na2SO4), then pooled, evaporated and purified by silica gel chromatography (CH2Cl2:MeOH/2:1) to provide 0.98 g of clear oil.

The synthetic route of tert-Butyl 4-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brewster, William Kirkland; Demeter, David Anthony; Erickson, William Randal; Klittich, Carla Jean Rasmussen; Lowe, Christian Thomas; Rieder, Brent Jeffrey; Nugent, Jaime Susanne; Yerkes, Carla Nanette; Zhu, Yuanming; Balko, Terry William; US2007/93498; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 58656-98-7, These common heterocyclic compound, 58656-98-7, name is tert-Butyl 4-fluorobenzoate, 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.

General procedure: 3-(2,6-Dichlorophenoxy)-1H-indazole (75.0 mg; 0.27 mmol; 1.00 eq.) and tetrahydrofuran (3.00 mL) were stirred at room temperature in a round bottom flask under nitrogen atmosphere. Sodium hydride 60% in mineral oil (21.5 mg; 0.54 mmol; 2.00 eq.) was added portion wise. After 15 minutes, methyl-6-chloro-nicotinic acid (92.2 mg; 0.54 mmol; 2.00 eq.) was added and the reaction mixture was stirred at 80 C for 16 hours. The reaction mixture was cooled and diluted with ethyl acetate (50 mL). The organic layer was washed with a saturated solution of NH4Cl (20 mL) and brine (20 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue, methanol (5.00 mL) were stirred in a round bottom flask. A 10 M solution of sodium hydroxyde (1.00 mL; 10.0 mmol; 37.2 eq.) was added and the reaction mixture was stirred at 50 C for 16 hours. The reaction mixture was cooled and diluted with ethyl acetate (20 mL) and water (10 mL). The pH of the aqueous layer was adjusted to 1 using a 3 M solution of hydrochloric acid. The aqueous layer was extracted with ethyl acetate (50 mL). The organic layers were dried over MgSO4, filtered and concentrated. The residue was purified using preparative LCMS.6-(3-(2,6-Dichlorophenoxy)-1H-indazol-1-yl)nicotinic acid was isolated as a beige solid (41.0 mg; 36.6%).

The synthetic route of 58656-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ouvry, Gilles; Bouix-Peter, Claire; Ciesielski, Fabrice; Chantalat, Laurent; Christin, Olivier; Comino, Catherine; Duvert, Denis; Feret, Christophe; Harris, Craig S.; Lamy, Laurent; Luzy, Anne-Pascale; Musicki, Branislav; Orfila, Danielle; Pascau, Jonathan; Parnet, Veronique; Perrin, Agnes; Pierre, Romain; Polge, Gaelle; Raffin, Catherine; Rival, Yves; Taquet, Nathalie; Thoreau, Etienne; Hennequin, Laurent F.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5802 – 5808;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 58656-98-7, 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 58656-98-7 as follows.

A Preparation of (26) where R10 is 2-Cyanoindole A mixture of 3.0 g (0.02 mol) of 2-cyanoindole, 4.2 g (0.02 mol) of tert-butyl-4-fluorobenzoate, and 5.5 g (0.04 mol) of potassium carbonate in 30 ml dimethyl sulfoxide was heated at 110 C. for 48 hours. The reaction was poured onto ice-water and extracted twice with ethyl acetate. The organic extracts were combined, washed with water and dried over magnesium sulfate. Evaporation yielded a dark oil which was flash chromatographed on silica gel, eluding with ethyl acetate-hexane 1:9 to give 3.6 g (0.011 mol) of 1-[4-(tertbutoxycarbonyl)phenyl]-2-cyanoindole as an oil.

According to the analysis of related databases, 58656-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Syntex (U.S.A.) Inc.; US5380739; (1995); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics