Category: 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. Formula: C7H3ClFN

To a solution of 2-chloro-4-fluoro-benzonitrile (4 g, 25.71 mmol) in DMF (20 mL) were added Na2S (3.01 g, 38.57 mmol). The mixture was held at room temperature with stirring on for 20 h. Then the mixture was added 1 M HCl to adjust to pH 6-7. MTBE (20 ml) and water (20 ml) was added. The aqueous phase was extracted with MTBE (20 mL X 2), the combined organic phases were washed with sat. NaHCC”3 (50 mL) and brine (50 mL), dried over anhydrous sodium sulphate. Removal of solvent gave a yellow solid (3.7 g). The residue was used to next step directly. m/z calcd for [C7H4CINS]” [M-H]~: 168.0; found: 168.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 60702-69-4, its application will become more common.

Reference:
Patent; GALECTO BIOTECH AB; BRIMERT, Thomas; JOHNSSON, Richard; LEFFLER, Hakon; NILSSON, Ulf; ZETTERBERG, Fredrik; (284 pag.)WO2016/120403; (2016); A1;,
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Reference 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.

The mixture of 2-chloro-3-fluorobenznitrile (28) (2.00 g,12.9 mmol), L-leucine (27a, 2.02 g, 15.4 mmol) and cesium carbonate(5.45 g, 16.7 mmol) in DMSO (60 mL) was stirred at 90 C for12 h. The mixture was extracted with aqueous NaHCO3 twice andaqueous phase was combined. The aqueous phase was acidifiedwith citric acid and extracted with EtOAc twice. The organic layerswere combined, washed with brine, dried over MgSO4 and concentratedin vacuo to give 29a (3.43 g, 12.9 mmol, 100%) as a brownoil. 1H NMR (300 MHz, CDCl3) d 0.96 (3H, d, J = 6.0 Hz), 1.01 (3H,d, J = 6.2 Hz), 1.65-1.88 (3H, m), 4.06-4.16 (1H, m), 4.50-4.62(1H, m), 6.50 (1H, dd, J = 8.6, 2.4 Hz), 6.65 (1H, d, J = 2.5 Hz), 7.42(1H, d, J = 8.5 Hz).

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:
Article; Aikawa, Katsuji; Asano, Moriteru; Ono, Koji; Habuka, Noriyuki; Yano, Jason; Wilson, Keith; Fujita, Hisashi; Kandori, Hitoshi; Hara, Takahito; Morimoto, Megumi; Santou, Takashi; Yamaoka, Masuo; Nakayama, Masaharu; Hasuoka, Atsushi; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3330 – 3349;,
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Electric Literature of 60702-69-4, The chemical industry reduces the impact on the environment during synthesis 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

Phenol (3.66 g, 39 mmol) dissolved in DMF (30 mL),It was treated with NaH 60% (1.56 g, 39 mmol) dispersed in oil in small portions until gas evolution ceased. The reaction mixture was stirred at room temperature for 10 minutes,Then 2-chloro-4-fluorobenzonitrile (2-A, 5.0 g, 32.5 mmol) was added. The mixtureStir for 3 hours at room temperature until completion (LCMS).Volatiles were removed in vacuo and the crude product was partitioned between DCM / water.The organic phase is separated, washed with saturated aqueous salt solution,Dried over Na2SO4.Concentration gave 7.5 g of an off-white solid.

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.

Reference:
Patent; Arqule, Inc; Lapierre, Jean-Marc; Eathiraj, Sudharshan; Namdev, Nivedita; Momose Takayuki, Brian; Ota, Yusuke; Momose, Takayuki; Tsunemi, Tomoyuki; Inagaki, Hiroaki; Nakayama, Kiyoshi; (35 pag.)JP2020/59741; (2020); A;,
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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

General procedure: To an ice-cooled solution of 12 (0.200 g, 0.979 mmol) in DMF (2.0 mL) was added NaH (60% in mineral oil, 0.047 g, 1.18 mmol), and the mixture was stirred at 0 C for 30 min. To the mixture was added 4-fluorobenzonitrile (0.237 g, 1.96 mmol), and the mixture was stirred at 0 C for 2 h and room temperature for 18 h. The mixture was acidified with saturated aqueous solution of NH4Cl 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). The product was recrystallized from hexane-EtOAc to give 3 (0.131 g, 44%) as white crystals.

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;,
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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. Recommanded Product: 2-Chloro-4-fluorobenzonitrile

Cool a solution of diisopropylamine (80.6 niL, 0.575 mol) in THF (1 L) to about -5 0C using an ice water/MeOH bath. Add /z-butyllithium (2.5 M in hexanes, 212 mL, 0.530 mol) dropwise over 1 h via a syringe pump (4 mL/min) while maintaining the reaction temperature between -5 to 0 0C during the addition. Stir the lithium diisopropylamide (LDA) solution for 1 h at 0 C and then transfer it via canula, over 1 h, to a -78 0C solution of 2-chloro-4-fluoro-benzonitrile (68.7 g, 0.442 mol) in THF (1 L). Allow the temperature of the reaction mixture to warm to about -65 0C during the initial addition of the LDA solution; however, keep the internal temperature below -70 0C during the remainder of the LDA addition. Keep the temperature of the resulting dark red-orange reaction mixture below -70 0C for 5 h and add iodomethane (251.2 g, 1.77 mol, ~3 mL/min) at such a rate that the reaction temperature is maintained below -65 0C during the addition. Allow the reaction mixture to slowly warm overnight. After stirring for 14 h, the temperature of the reaction mixture is -5 0C. Quench the reaction with saturated aqueous ammonium chloride (500 mL) and water (750 mL) and dilute with diethyl ether (about 2 L). Separate the layers and extract the aqueous layer with diethyl ether (about 1 L). Dry the combined organic layer (about 5.5 L) over MgSO4, filter, and concentrate to afford the crude title compound as a red-brown oily solid (about 86.7 g). Subject the crude residue (dry loaded on silica gel using methylene chloride) to flash chromatography (silica gel (10 x 30 cm), gradient of 99: 1 to 93:7 hexane/EtOAc) to obtain the title compound (56.7 g, 76%) as a white solid, m.p. 63 – 65 0C; 1H NMR (300 MHz, CDCl3): delta 7.54 (dd, J= 8.6, 5.6 Hz, IH), 7.08 (dd, J = 8.6, 8.6 Hz , IH), 2.36 (d, / = 2.4 Hz, 3H).

The synthetic route of 2-Chloro-4-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/124447; (2006); A2;,
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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. 60702-69-4

To a solution of (4S,5S)-4-hydroxy-5-methylpyrrolidin-2-one 7 33 (7.00 g, 60.8 mmol) in THF (120 mL) was added sodium bis(2-methoxyethoxy)aluminium dihydride (70% in toluene, 59.7 mL, 215 mmol) slowly at 5 C. After stirring at 70 C for 3 h, the reaction mixture was cooled to 5 C followed by addition of sodium carbonate decahydrate (26.1 g, 91.2 mmol). The mixture was stirred at room temperature for 16 h, diluted with THF, and the precipitate was filtered off. The filtrate was concentrated in vacuo, and the residue was dissolved in DMSO (80 mL). To the solution was added lithium carbonate (8.99 g, 122 mmol) and 2-chloro-4-fluorobenzonitrile (9.46 g, 60.9 mmol), and the mixture was stirred at 100 C for 1 h. The mixture was diluted with EtOAc and H2O, and the organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc) to give 10 (10.7 g, 74%) as a colorless solid. 1H NMR (300 MHz, CDCl3) delta: 1.18 (3H, d, J = 6.6 Hz), 1.82 (1H, d, J = 5.5 Hz), 2.01-2.14 (1H, m), 2.25-2.35 (1H, m), 3.19-3.28 (1H, m), 3.43-3.51 (1H, m), 3.89-3.98 (1H, m), 4.43-4.52 (1H, m), 6.43 (1H, dd, J = 8.9 and 2.4 Hz), 6.56 (1H, d, J = 2.4 Hz), 7.42 (1H, d, J = 8.9 Hz). MS (ESI) m/z 237 [(M+H)+].

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.

Reference:
Article; Yamamoto, Satoshi; Kobayashi, Hiromi; Kaku, Tomohiro; Aikawa, Katsuji; Hara, Takahito; Yamaoka, Masuo; Kanzaki, Naoyuki; Hasuoka, Atsushi; Baba, Atsuo; Ito, Mitsuhiro; Bioorganic and Medicinal Chemistry; vol. 21; 1; (2013); p. 70 – 83;,
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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.

Synthesis of tert-butyl N-[(1r,4r)-4-(3-chloro-4-cyanophenoxy)cyclohexyl]carbamate Into a 50.0-mL round-bottom flask, was placed tert-butyl N-[(1r,4r)-4-hydroxycyclohexyl]carbamate (500.0 mg, 2.32 mmol, 1.00 equiv), N,N-dimethylformamide (10.0 mL), sodium hydride (82.8 mg, 3.45 mmol, 1.50 equiv), 2-chloro-4-fluorobenzonitrile (432.6 mg, 2.78 mmol, 1.20 equiv). The resulting solution was stirred for 2 hours at 0 C. in a water/ice bath. The reaction was then quenched by the addition of 20.0 mL of water. The resulting solution was extracted with ethyl acetate (40.0 mL) and the organic layers combined. The resulting mixture was washed with sodium chloride (40.0 mL). The mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/2). The collected fractions were combined and concentrated under vacuum. This resulted in 470.0 mg (58%) of tert-butyl N-[(1r,4r)-4-(3-chloro-4-cyanophenoxy)cyclohexyl]carbamate as yellow oil. LC-MS (ES+): m/z 295.0 [MH+], tR=1.199 min, (1.90 minute run).

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.

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;,
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The chemical industry reduces the impact on the environment during synthesis 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, I believe this compound will play a more active role in future production and life. 60702-69-4

Example 34A(2Z)-3-Amino-3-(2-chloro-4-fluorophenyl)prop-2-enonitrile; Under argon, 35.3 g (273 mmol) of diisopropylamine were initially charged in 450 ml of THF at -70 C. in a three-necked flask with mechanical stirrer. 145 ml of N-butyllithium solution (1.6 M in hexane, 237 mmol) were added dropwise at such a rate that the temperature did not exceed -60 C. The mixture was stirred for 30 min, and a solution of 12.7 ml (241 mmol) of acetonitrile in 100 ml of THF was then slowly added dropwise and the suspension was stirred for 30 min. A solution of 25 g (160.7 mmol) of 2-chloro-4-fluorobenzonitrile in 100 ml of THF was added dropwise, and the mixture was stirred at -70 C. for 20 min. The mixture was allowed to slowly warm to RT and stirred at RT for a further 16 h. 150 ml of water were added, most of the THF was distilled off and water and dichloromethane were added. The organic phase was washed with saturated aqueous sodium chloride solution. Removal of the solvent gave an oil. A solid could be obtained by trituration with diisopropylether and subsequent filtration with suction. Drying under high vacuum gave 12.58 g (36% of theory) of the product. This was a mixture of E and Z isomers which was used without further purification.LCMS (Method 8): Rt (isomer 1)=0.83 min. (m/z=197 (M+H)+); Rt (isomer 2)=1.02 min. (m/z=197 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=7.52 (dd, 1H), 7.44 (dd, 1H), 7.26 (m, 1H), 6.99 (s, br, 2H), 3.77 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 60702-69-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLESCHAFT; US2011/144131; (2011); A1;,
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