Category: 75279-53-7

Adding a certain compound to certain chemical reactions, such as: 75279-53-7, name is 4-Chloro-2-fluorobenzeneacetonitrile, belongs to nitriles-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 75279-53-7, Application In Synthesis of 4-Chloro-2-fluorobenzeneacetonitrile

To a solution of 4-chloro-2-fluoro-benzyl cyanide (Oakwood) (1.70 g, 10.0 mmol) and 3,3-dimethyl-butyraldehyde (Aldrich) (1.0 g, 10.0 mmol) in iPrOH (20 mL) was added 2 N NaOH (2.0 mL) dropwise at rt and the reaction mixture was stirred at rt overnight. The reaction mixture was diluted with EtOAc and the organic layer was separated, washed with water, brine, dried over Na2SO4 and concentrated. The residue was dried overnight in vacuum to give (Z)-2-(4-chloro-2-fluoro-phenyl)-5,5-dimethyl-hex-2-enenitrile (2.52 g, 100%) as a colorless oil which was used in the next step without further purification.

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

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Liu, Jin-Jun; Morgan Ross, Tina; Zhang, Zhuming; US2011/86854; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 75279-53-7, name is 4-Chloro-2-fluorobenzeneacetonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 75279-53-7

Intermediate 36: tert-Butyl 4-((4-chloro-2-fluorophenyl)(cyano)methyl)piperidine-1-carboxylate A solution of 2-(4-chloro-2-fluorophenyl)acetonitrile (0.353 g, 2.082 mmol) in DMF (5 mL) was cooled to 0-5 C., to this was added sodium hydride (0.050 g, 2.082 mmol) and tert-butyl 4-bromopiperidine-1-carboxylate (0.5 g, 1.893 mmol). The reaction was stirred at room temperature for 3 hours. The mixture was quenched with ice/water and partitioned between ethyl acetate and water. The phases were separated and the aqueous extracted with ethyl acetate. The combined organics were washed with water, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography on silica, eluted with 0-50% ethyl acetate/petroleum ether to afford ten-butyl 4-((4-chloro-2-fluorophenyl)(cyano)methyl)piperidine-1-carboxylate (0.5 g, 75%).

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; Carroll, Colm; Goldby, Anne; Teall, Martin; US2013/324576; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 75279-53-7, name is 4-Chloro-2-fluorobenzeneacetonitrile, belongs to nitriles-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 75279-53-7, Safety of 4-Chloro-2-fluorobenzeneacetonitrile

To a solution of 4-chloro-2-fluorophenylacetonitrile (Matrix) (5 g, 30 mmol) and 3-chloro-2-fluorobenzaldehyde (Oakwood) (5 g, 32 mmol) in methanol (200 mL) was slowly added a methanolic solution (Aldrich, 25 wt. %) of sodium methoxide (21 mL, 92 mmol). The reaction mixture was heated and stirred at 45 C. for 5 h. The mixture was cooled to room temperarure and filtered. The white precipitate was washed with water, cold methanol, and then dried under reduced pressure to afford (Z)-3-(3-chloro-2-fluoro-phenyl)-2-(4-chloro-2-fluoro-phenyl)-acrylonitrile as a white powder (8 g, 86%).

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

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Liu, Jin-Jun; Morgan Ross, Tina; Zhang, Zhuming; US2011/86854; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 75279-53-7, A common heterocyclic compound, 75279-53-7, name is 4-Chloro-2-fluorobenzeneacetonitrile, molecular formula is C8H5ClFN, 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.

Reagents and conditions: (a) EtONa, EtOH, refluxing; (b) CH3NHNH2, HC1, EtOH, IVIW, 100C, 40 mm; (c) 2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)acetic acid,Mukaiyama?s reagent, TEA, DCM, THF, MW, 75C, 30 mm. A mixture of 1.8 ml (15mmol) of ethyl 2,2,2-trifluoroacetate (ib) and 1.2 g (7.1 mmol) of 2-(4-chloro-2-fluorophenyl)acetonitrile (la) in 10 ml of ethanol was slowly dropped into hot solutionof 1.2 g of sodium in 20 ml of ethanol. The mixture was refluxed overnight. Thesolution turns red. After cooled down, the solution was poured into 250 ml of cold wateracidified with 10 ml concentrated HC1. The mixture was extracted with ethyl acetate.The ethyl acetate extraction was washed with water, brine and dried over MgSO4. Ethylacetate was removed and the residual reddish oil of 2-(4-chloro-2-fluorophenyl)-4,4,4-trifluoro-3-oxobutanenitrile (ic) was obtained in 1.2 g. The raw material was dissolvedin 10 ml of ethanol and used in next step without further purification. A mixture of 2 mlof the above ethanol solution and 72 tl of methylhydrazine with 0.14 ml ofconcentrated HC1 was irradiated in microwave oven at 100C for 40mm. The solutionwas treated with saturated NaHCO3 and extracted by ethyl acetate. The organic layerwas washed with water, brine, dried over MgSO4 and concentrated. The yellow residuewas subjected to flash chromatography purification with MeOHIDCM to give 120 mgof 4-(4-chloro-2-fluorophenyl)-3 -(trifluoromethyl)- 1-methyl-i H-pyrazol-5 -amine (id)as light yellow solid. M/Z = 294.6 (M+i). To a mixture of 2-(2-isopropyl-1H-benzo[d]imidazol-i-yl)acetic acid (0.16 mmol, from ChemBridge) and Mukaiyama?sreagent (0.38 mmol) in 1.5 ml anhydrous DCM, 4-(4-chloro-2-fluorophenyl)-3-(trifluoromethyl)- i-methyl-i H-pyrazol-5 -amine (1 d, 0.12 mmol) obtained as described above, triethylamine (0.40 mmol) and 0.5 ml of anhydrous THF were added. The mixture was vortexed and subject to microwave irradiation for 30 mm at 75C to give a deep green clear solution. Then 80 ml of ethyl acetate was added and washed with 80 ml of saturated NaHCO3 twice, brine and dried over MgSO4. After solvent removal andpurification on a flash chromatography, slightly brown color solid was obtained. After recrystallization in ethyl acetate/hexane, 45 mg of Compound (1) was given as white powder solid. ?HNMR (500 MFIz, MeOD) 7.79 (d, J = 7.7 Hz, 1H), 7.62 (dt, J = 15.8, 8.2 Hz, 3H), 7.36 – 7.15 (m, 3H), 5.55 (s, 2H), 3.89 (s, 3H), 3.55 – 3.44 (m, 1H), 1.47 (d, J = 6.9 Hz, 6H); M/Z =494.9 (M+1).

The synthetic route of 75279-53-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; DREXEL UNIVERSITY; UNIVERSITY OF WASHINGTON; BURROWS, Jeremy; WYVRATT, Matthew; VAIDYA, Akhil; KORTAGERE, Sandhya; FAN, Erkang; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; KATO, Tomoyo; WO2015/8246; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 75279-53-7, name is 4-Chloro-2-fluorobenzeneacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H5ClFN

To a mixture of 3-chloro-2-fluoro-benzaldehyde (13.7 g, 86.68 mmol, 1.05 eq) and 2- (4-chloro-2-fluoro-phenyl)acetonitrile (14 g, 82.56 mmol, 1 eq) in methanol (200 mL) was added the solution of sodium methoxide (13.4 g, 247.67 mmol, 3 eq) in methanol (40 mL) dropwise at 0 C under nitrogen atmosphere. The product begins to precipitate during the addition. The suspension was stirred at 45 C for 5 hours. The solid was filtered and washed with water (200 mL) and methanol (50 mL) and then was dried in vacuum to give (Z)-3-(3-chloro-2-fluoro- phenyl)-2-(4-chloro-2-fluoro-phenyl)prop-2-enenitrile (24 g, 77.39 mmol, 93% yield) as a white solid. 1H-NMR (400MHz, CDCL) d 8.20 – 8.10 (m, 1H), 7.81 (s, 1H), 7.64 – 7.49 (m, 2H), 7.33 – 7.20 (m, 3H).

According to the analysis of related databases, 75279-53-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARVINAS OPERATIONS, INC.; YALE UNIVERSITY; CREW, Andrew P.; HORNBERGER, Keith R.; WANG, Jing; DONG, Hanqing; BERLIN, Michael; CREWS, Craig M.; (1213 pag.)WO2019/195609; (2019); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 75279-53-7 as follows. COA of Formula: C8H5ClFN

A solution of 4-chloro-2-fluorobenzeneacetonitrile (0.059 mol) in anhydrous DMF (150 ml) was chilled on an ice-bath. t-BuOK (0.118 mol) was added under nitrogen and the resulting mixture was stirred for 30 minutes. l,2-Dichloro-4-methyl-5- nitrobenzene (0.059 mol) was added and the reaction mixture was stirred for 1 hour at 00C. The mixture was allowed to warm to room temperature for 1 hour and then cooled to 00C. A solution of hydrogen peroxide in water (30%) (17.8 ml) was added and air was bubbled through the solution overnight. The obtained mixture was slowly added dropwise to IN HCl (750 ml) and after stirring in ice-cold DIPE, the resulting precipitate was filtered off, yielding 5.83 g of intermediate (1).

According to the analysis of related databases, 75279-53-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2008/152081; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts