Category: 60702-69-4

60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C7H3ClFN

To an ice-cooled mixture of 23 (0.100 g, 0.485 mmol) and DMF (1.0 mL) was added NaH (60% in mineral oil, 0.023 g, 0.582 mmol), and the mixture was stirred at 0 C for 30 min. To the mixture was added 2-chloro-4-fluorobenzonitrile (0.151 g, 0.970 mmol), and the mixture was stirred at 0 C for 1 h. The mixture was mixed with saturated aqueous solution of NaHCO3 and extracted twice with EtOAc. The organic layers were combined, washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc) to afford 25 (0.088 g, 53%) as a white solid, mp 118-119 C. 1H NMR (300 MHz, CDCl3) delta: 2.13 (3H, s), 2.32 (3H, s), 6.82-6.91 (2H, m), 6.96-7.05 (2H, m), 7.55 (1 H, dd, J = 8.7 and 1.9 Hz), 7.72-7.81 (2H, m). Anal. Calcd for C18H13ClFN3O: C, 63.26; H, 3.83; N, 12.29. Found: C, 63.22; H, 3.78; N, 12.35.

The synthetic route of 60702-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yamamoto, Satoshi; Tomita, Naoki; Suzuki, Yuri; Suzaki, Tomohiko; Kaku, Tomohiro; Hara, Takahito; Yamaoka, Masuo; Kanzaki, Naoyuki; Hasuoka, Atsushi; Baba, Atsuo; Ito, Mitsuhiro; Bioorganic and Medicinal Chemistry; vol. 20; 7; (2012); p. 2338 – 2352;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 60702-69-4, 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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 23A; 2-chloro-4-fluoro-5-nitrobenzonitrile; To a solution of 2-chloro-4-fluorobenzonitrile (10.1 g, 64.9 mmol) in concentrated sulfuric acid (20 mL) was added fuming nitric acid (5.80 ml, 130 mmol) at room temperature slowly and the mixture was stirred for 60 minutes. The solution was then poured into ice-water and stirred for 20 minutes. The precipitate was filtered, washed with more water and air-dried to afford the crude material, which was purified by sublimation to afford the title compound. .H NMR (300 MHz, dimethylsulfoxide-d6) delta ppm 8.97 (d, J = 8.09 Hz, 1 H) 8.30 (d, J = 11.03 Hz, 1 H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; XU, Xiangdong; DINGES, Jurgent; HASVOLD, Lisa; LONGENECKER, Kenton, L.; WO2012/45196; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 60702-69-4, 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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

1. Synthesis of tert-butyl N-[(1r,3r)-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamate Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl N-[(1r,3r)-3-hydroxy-2,2,4,4-tetramethylcyclobutyl]carbamate (600.0 mg, 2.47 mmol, 1.00 equiv) in N,N-dimethylformamide (10.0 mL). This was followed by the addition of sodium hydride (198.0 mg, 8.25 mmol, 2.00 equiv), in portions at 0 C. After 30 minutes, to this was added 2-chloro-4-fluorobenzonitrile (459.0 mg, 2.95 mmol, 1.20 equiv). The resulting solution was stirred for 1 hour at 70 C. The reaction mixture was cooled to room temperature with a water bath. The reaction was then quenched by the addition of water (20 mL). The resulting solution was extracted with ethyl acetate (20 mL*3) and the organic layers combined. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/5). This resulted in 100.0 mg (11%) of tert-butyl N-[(1r,3r)-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamate as colorless oil. LC-MS (ES+): m/z 279.10 [MH-100]+, tR=1.20 min (2.5 minute run).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 60702-69-4,Some common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, molecular formula is C7H3ClFN, 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.

(Step 3) To a solution of the compound obtained in Step 2 (500 mg, 1.54 mmol) and 2-chloro-4-fluorobenzonitrile (240 mg, 1.54 mmol) in THF (15 mL) was added potassium t-butoxide (432 mg, 3.85 mmol) at room temperature, and the mixture was stirred for 14 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 75% ethyl acetate/hexane) to give the title compound (458 mg, 0.996 mmol, 64.6%) as a colorless powder. 1H-NMR (300MHz,DMSO-d6):delta1.03 (3H,d,J=6.0Hz), 1. 20-1.42(3H,m), 1.56-1.79(1H,m), 1.79-2.00(1H,m), 2.14-2.33(2H,m), 2.33-2.48(1H,m), 4.04-4.31(2H,m), 4.41(2H,q,J=6.9Hz), 7.00-7.26(2H,m), 7.35(1H,d,J=2.3Hz), 7.38-7.49(1H,m), 7.49-7.66(3H,m), 7.85(1H,d,J=8.7Hz), 8.04(1H,d,J=7.9Hz), 8.40(1H,s), 9.91(1H,s).

The synthetic route of 60702-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; FUKASE, Yoshiyuki; TOMATA, Yoshihide; SATO, Ayumu; OCHIDA, Atsuko; YONEMORI, Kazuko; NAKAGAWA, Hideyuki; EP2759533; (2014); 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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Chloro-4-fluorobenzonitrile

Reference Example 112 N-(3-chloro-4-cyanophenyl)-4-fluorophenylalanine To a solution of 2-chloro-4-fluorobenzonitrile (1.8 g) in dimethyl sulfoxide (30 mL) were added 4-fluorophenylalanine (2.54 g) and cesium carbonate (4.90 g), and the mixture was stirred at 90 C. overnight. After allowing to room temperature, ethyl acetate was added, and the mixture was extracted twice with saturated aqueous sodium hydrogen carbonate solution. The aqueous layers were combined, and acidified with citric acid, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound as a brown oil (yield: 3.69 g, 100%). 1H-NMR(CDCl3)delta:3.07-3.30(2H,m), 4.40(1H,q,J=5.9 Hz), 4.72(1H,d,J=6.6 Hz), 6.46(1H,dd,J=8.7,2.3 Hz), 6.60(1H,d,J=2.3 Hz), 6.94-7.05(2H,m), 7.07-7.16(2H,m), 7.41(1H,d,J=8.7 Hz).

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 60702-69-4.

Application of 60702-69-4, These common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, 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.

Combine the compound from Example 218 step 2 (692 mg, 2.12 mmol) and K2CO3 (323 mg, 2.33 mmol) in DMF (9 mL), stir the mixture at room temperature for 30 min and then add 2-chloro-4-fluoro-benzonitrile (330 mg, 2.12 mmol), and heat at 100 C overnight. Cool to ambient temperature and pour into water. Extract the aqueous layer with EtOAc. Dry the organic layer over NA2SO4 and eliminate the solvent. Purify by flash chromatography on silica gel (eluent: ETOAC/HEXANE 15/85) to obtain the title compound (940 mg, 95%). Electrospray MS M-1 ion = 461, H-NMR (CDC13, 400 MHz): 7.57 (d, 1H, J= 7.8 Hz), 7.36-7. 13 (m, 7H), 7. 00-6. 85 (m, 4H), 4.44-4. 36 (M, 2LI) 3.49-3. 32 (m, 2H), 2.83-2. 73 (m, 2H), 1.51-1. 43 (m, 9H).

Statistics shows that 2-Chloro-4-fluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 60702-69-4.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/26305; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 60702-69-4, 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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 11 2-Chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)-3-iodobenzonitrile (195JP18) Adapting a protocol by Uchiyama et al (J. Am. Chem. Soc., 2002, 124, 8514-8515), which reference is incorporated herein by reference in its entirety, 2-chloro-4-fluorobenzonitrile (311 mg, 2.0 mmol) in dry THF (1.0 mL) was added dropwise to lithium di-t-butyl(2,2,6,6-tetramethylpiperidino)zinncate (4.0 mmol in 10 mL THF, Uchiyama et al J. Am. Chem. Soc., 1999, 121, 3539-3540, which is incorporated herein by reference in its entirety) at 0 C. and stirred at 0 C. for 3.5 h. Iodine (5.08 g, 20.0 mmol) was then added and the reaction was stirred at r.t. overnight. Na2S2O3 (1.0 M, 50 mL) and saturated aqueous NH4Cl (100 mL) were added, followed by extraction with dichloromethane (3*100 mL), drying of the combined organic layers over Na2SO4, filtering, and removal of the solvents in vacuo. The residue was passed through a pad of silica gel eluding with EtOAc/n-heptane (1:40), affording 112 mg (0.40 mmol) of 2-chloro-4-fluoro-3-iodobenzonitrile. This material was combined with nortropine (114 mg, 0.90 mmol), K2CO3 (186 mg, 0.134 mol) and DMSO (2.0 mL), and stirred at 130 C. for 1.5 h. The crude mixture thus obtained was diluted with n-heptane (10 mL), passed through a pad of silica gel using EtOAc/n-heptane (1:2), concentrated and purified by preparative TLC (EtOAC/n-heptane, 1:1) to give 1.5 mg (1.7%) of 195JP18 as an off-white solid. Rf=0.21 (EtOAc/n-heptane 1:1). LC/MS m/z 389 [M+H]+. 1H-NMR (CDCl3) delta 7.42 (d, 1H, J=8.6), 6.70 (d, 1H, J=8.6), 4.16 (br s, 1H), 3.95 (br s, 2H), 2.50-2.22 (m, 4H) 1.93-1.78 (m, 4H).

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

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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H3ClFN

a) (2S)-2-[(3-Chloro-4-cyanophenyl)amino]-4-[(1,1-dimethylethyl)oxy]-4-oxobutanoic acid2-Chloro-4-fluorobenzonitrile (2.13 g, 13.8 mmol), (2S)-2-amino-4-[(1,1-dimethylethyl)oxy]-4-oxobutanoic acid (2.6 g, 13.8 mmol) and NaHCO3 (3.5 g, 41.4 mmol) in DMSO (70 mL) and H2O (10 mL) were stirred at 95 C. for 15 h. After cooling, the reaction mixture was diluted with H2O (100 mL) and washed with Et2O (100 mL). The H2O layer was acidified to Congo Red midpoint and extracted with Et2O (2¡Á). The combined organic extracts were washed with H2O, dried over Na2SO4, filtered, and concentrated to give the titled product (3.59 g, 80%) as a foam. 1H-NMR (CDCl3) delta: 1.45 (9H, s), 2.89 (2H, m), 3.54 (1H, m), 4.42 (1H, m), 6.55 (1H, d, J=8.8 Hz), 6.70 (1H, s), 7.43 (1H, d, J=8.4 Hz). LC-MS (ES) m/e 325.4 (M+H)+.

According to the analysis of related databases, 60702-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WASHBURN, David G.; HOANG, Tram H.; US2008/39517; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, 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 60702-69-4, Computed Properties of C7H3ClFN

To a cooled suspension of NaH (60% in mineral oil, 6.24 g, 156 mmol) in DMF (100 mL) at 5 C was added 3,5-dimethylpyrazole 30 (15.0 g, 156 mmol) dropwise. After stirring at 5 C for 30 min, 2-chloro-4-fluorobenzonitrile (24.3 g, 156 mmol) was added dropwise, and the whole was stirred at 0 C for 1 h. The mixture was diluted with water. The resulting precipitates were collected by filtration, washed with water and hexane, and dried in air. The resulting solid was purified by silica gel column chromatography (NH silica gel, hexane-EtOAc). The product was recrystallized from hexane-EtOAc to afford 31 (21.0 g, 58%) as a colorless powder. 1H NMR (300 MHz, CDCl3) delta: 2.29 (3H, s), 2.42 (3H, s), 6.07 (1H, s), 7.51 (1H, dd, J = 8.5 and 2.1 Hz), 7.70-7.76 (2H, m).

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

Reference:
Article; Yamamoto, Satoshi; Tomita, Naoki; Suzuki, Yuri; Suzaki, Tomohiko; Kaku, Tomohiro; Hara, Takahito; Yamaoka, Masuo; Kanzaki, Naoyuki; Hasuoka, Atsushi; Baba, Atsuo; Ito, Mitsuhiro; Bioorganic and Medicinal Chemistry; vol. 20; 7; (2012); p. 2338 – 2352;,
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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3ClFN

Preparation 12-Chloro-4-fluoro-3-methyl-benzonitrileTo a solution of diisopropylamine (474 mL, 3.35 mol) in anhydrous THF (5.8 L) at-5 C under a nitrogen atmosphere is added dropwise 2.5 M n-butyllithium in hexanes (1.24 L, 3.10 mol) over 3 h and the resulting mixture is stirred at -5 C for one additional hour. The LDA solution is added dropwise to a solution of 2-chloro-4-fluoro-benzonitrile (400 g, 2.58 mol) in anhydrous THF (5.8 L) at -70 C over 6 h and then stirred at -70 C overnight. lodomethane (643 mL, 10.32 mol) is added dropwise over 2.5 h and the temperature is raised to -5 C for 17 h. Saturated aqueous ammonium chloride (3 L) is added. The solution is diluted with water (3.5 L) and extracted with diethyl ether (2 x 2 L). The organic phases are separated, combined, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a black solid. The solid is purified through a silica gel pad eluting withEtOAc/hexanes (1/40) to obtain the title compound (323 g, 74%). 1H NMR (300 MHz, CDCls) delta 7.08 (dd, J= 8.6, 8.6 Hz, 1H), 7.54 (dd, J= 8.6, 5.6 Hz, 1H), 2.36 (d, J= 2.4 Hz, 3H).

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; ELI LILLY AND COMPANY; JADHAV, Prabhakar Kondaji; SAEED, Ashraf; GREEN, Jonathan Edward; KRISHNAN, Venkatesh; MATTHEWS, Donald Paul; STEPHENSON, Gregory Alan; WO2013/55577; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts