Category: 20154-03-4

Synthetic Route of 20154-03-4, A common heterocyclic compound, 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, molecular formula is C4H3F3N2, 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.

Reference Example 15 Preparation of 2-Chloro-4-(3-trifluoromethylpyrazolyl)benzaldehyde (Compound XVI) 4.08 g (30.0 mmol) of 3-trifluoromethylpyrazol, 4.75 mmol (30.0 mmol) of 2-chloro-4-fluorobenzaldehyde and 4.14 g (30.0 mmol) of potassium carbonate in 30 ml of N,N-dimethylformamide were stirred at 60° C. for 2 hours. After cooling to room temperature, the reaction mixture was poured into 100 ml of water, and the organic matters were extracted with 50 ml of ethyl acetate twice. The ethyl acetate layers were combined, washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. The residue afforded 7.18 g of 2-chloro-4-(3-trifluoromethylpyrazolyl)benzaldehyde (yield 87.2percent) as a pale yellow powder, after washed with n-hexane.

The synthetic route of 20154-03-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US6509354; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H3F3N2

Step 1: Into a 50 mL round bottom flask were added 3-(trifluoromethyl)-1H-pyrrazole (5.0 g, 33 mmol), sulfuric acid (25 mL) and nitration mixture (sulfuric acid and fuming nitric acid, 25 mL/ 25 mL) and the reaction was stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water and saturated sodium bicarbonatesolution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure.The residue was purified by flash column chromatography eluting with ethyl acetate inpetroleum ether (20-30%) to furnish 4-nitro-3-(trifluoromethyl)-1H-pyrazole as a solid. ?HNMR(CDC13, 400 MHz): 11.66 (brs, 1H), 8.47 (s, 1H). MS calc?d [M-Hj 180.0, found180.0.

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 20154-03-4.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; BRUBAKER, Jason, D.; GIBEAU, Craig, R.; (187 pag.)WO2016/144846; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 20154-03-4, 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 20154-03-4 as follows.

To a stirred solution of 10 g (73.5 mmol) 3-(trifluoromethyl)-1H-pyrazole (3) in DMSO (150 ml) were added 9.9 g of potassium tert.-butoxide portion wise. After stirring for 5 minutes drop wise addition of 12 ml of iodoethane followed by stirring overnight were conducted. Water was added afterwards and the pH value was adjusted to 3 by using 1N HCl. The mixture was diluted with MTBE and extracted two more times with MTBE. The combined organic phase was washed with Na2S2O3-solution, water and brine yielding 8 g (67 percent) of the ionic liquid 8.

According to the analysis of related databases, 20154-03-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOLVAY SA; Braun, Max Josef; Fischer, Reiner; EP2662359; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, 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. Recommanded Product: 3-(Trifluoromethyl)-1H-pyrazole

NaH (33.08 g (19.85, 60percent), 1.5 eq) was added to small quantity of hexane and stirred well for 10 min. Hexane was decanted, dry DMF (500 ml) was added drop wise under N2 atmosphere and stirred well. A solution of step-b product (75 g, 0.55 mol) in DMF (125 ml) was added drop wise under N2 atmosphere. Then a solution of 4-methoxylbenzoyl chloride (86.3 g, 0.55 mol, 1 eq) in DMF (125 ml) was added drop wise and the overall reaction mixture was allowed to stir for 12 hrs at RT. Progress of the reaction was monitored by TLC (10percent ethyl acetate/hexane, Rf-0.4). On completion of the reaction, reaction contents were poured into ice water (500 ml) and the product extracted with ethyl acetate (2 * 400 ml). Then the contents were dried over sodium sulfate and concentrated under reduced pressure to yield the required product as a brown colored liquid (125 g, 88percent yield).

The synthetic route of 3-(Trifluoromethyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; SCHIENE, Klaus; DE VRY, Jean; DAMANN, Nils; FRORMANN, Sven; LESCH, Bernhard; LEE, Jeewoo; KIM, Yong-Soo; KIM, Myeon-Seop; WO2010/127856; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – 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. 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C4H3F3N2

Step A: Preparation of 2-chloro-4-[3-(trifluoromethyl)-lH-pyrazol-l-yl]benzaldehyde A mixture of 2-chloro-4-fluorobenzaldehyde (7.0 g, 44.3 mmol), 3-(trifluoromethyl)- lH-pyrazole (9.03 g, 66.45 mmol) and potassium carbonate (12.2 g, 88.6 mmol) in anhydrous N,N-dimethylformamide (70 mL) was stirred for 2 h at 110 °C. The reaction mixture was cooled to 0 °C, poured into ice water (800 mL) and stirred for 15 min. The precipitate formed was filtered and dried under reduced pressure to afford the title compound (10.2 g), which was used without further purification. H NMR delta 10.4 (s, 1H), 8.00 (m, 2H), 7.85 (d, 1H), 7.77 (m, 1H), 6.70 (d, 1H).

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; E. I. DU PONT DE NEMOURS AND COMPANY; BEREZNAK, James, Francis; TAGGI, Andrew, Edmund; MARCUS, Kimberly, Katherine; REDDY, Ravisekhara, P.; WO2014/172191; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 20154-03-4,Some common heterocyclic compound, 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, molecular formula is C4H3F3N2, 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 3-trifluoromethylpyrazole (5.0 g, 36 mmol), triethylamine (7.0 mL, 50 mmol) in dichloromethane (40 mL) was added dimethylsulfamoyl chloride (5.5 mL, 51 mmol), and the reaction mixture was heated at reflux for 2 days. The resulting mixture was cooled to ambient temperature and filtered through a pad of silica gel using dichloromethane as eluent. The filtrate was then concentrated under reduced pressure to give an amber residue. The resulting residue was dissolved in diethyl ether. The ether solution was washed with water, dried (MgSC^), and concentrated under reduced pressure to give 8.71 g of the title compound. 1HNMR (CDCl3) delta 3.01 (s, 6H), 6.65 (s, IH)5 8.03 (s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Trifluoromethyl)-1H-pyrazole, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2008/13622; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 3-(Trifluoromethyl)-1H-pyrazole

Step A: Preparation of N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide To a solution of 3-trifluoromethylpyrazole (5.0 g, 36 mmol), triethylamine (7.0 mL, 50 mmol) in dichloromethane (40 mL) was added dimethylsulfamoyl chloride (5.5 mL, 51 mmol), and the reaction mixture was heated at reflux for 2 days. The resulting mixture was cooled to ambient temperature and filtered through a pad of silica gel using dichloromethane as eluent. The filtrate was then concentrated under reduced pressure to give an amber residue. The resulting residue was dissolved in diethyl ether. The ether solution was washed with water, dried (MgSO4), and concentrated under reduced pressure to give 8.71 g of the title compound. 1H NMR (CDCl3): delta 3.01 (s, 6H), 6.65 (s, 1H), 8.03 (s, 1H).

The synthetic route of 20154-03-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gregory, Vann; Pasteris, Robert James; US2010/240619; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 20154-03-4, 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. 20154-03-4 name is 3-(Trifluoromethyl)-1H-pyrazole, 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.

Step 1: Preparation of 4-iodo-3-(truoromethyl)-1H-pyrazole. To a solution of 3- (trifluoromethyl)-1H-pyrazole (500 mg, 3.7 mmol) in 50percent 112S04 at 0 °C was added MS (992 mg, 4.4 mmol). The suspension was stirred at 0°C for 10 mm and then at r.t. for 3 hr. The resulting mixture was quenched with water (50 mL), and then stirred overnight. The precipitate was collected by filtration and dried to afford 4-iodo-3-(trifluoromethyl)-1H-pyrazole.LC-MS:m/z 263 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(Trifluoromethyl)-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; KONTEATIS, Zenon D.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; ZAHLER, Robert; CAI, Zhenwei; ZHOU, Ding; WO2015/3640; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 20154-03-4,Some common heterocyclic compound, 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, molecular formula is C4H3F3N2, 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 3-trifluoromethyl-1H-pyrazole (500 mg, 3.67 mmol) in glacial acetic acid (5 ml) was added a 10percent solution of sodium hypochlorite in water (2188 mul, 3.67 mmol). The reaction mixture was stirred at RT overnight and then neutralized with sat. sodium carbonate, and extracted with DCM. The organic layers were combined washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give the desired product (480 mg, 77percent) as a white solid which did not require further purification. MS (ISP) 169.0 (M-H)-.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Trifluoromethyl)-1H-pyrazole, its application will become more common.

Reference:
Patent; Conte, Aurelia; Kuehne, Holger; Luebbers, Thomas; Mattei, Patrizio; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe; US2007/185058; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 20154-03-4, 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. 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1?3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5?10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C?N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

The chemical industry reduces the impact on the environment during synthesis 3-(Trifluoromethyl)-1H-pyrazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics