Category: 3939-09-1

Synthetic Route of 3939-09-1, These common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, 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.

Step A – Synthesis of Intermediate Compound Int-2a To a solution of NaH (1.2 g, 30 mmol) in toluene (50 mL) was added but-3-en-l- ol (1.8 g, 25 mmol) dropwise and the mixture was allowed to stir at room temperature for 30 minutes. 2,4-Difluorobenzonitrile (4.2 g, 30 mmol) was then added in one portion and the mixture was allowed to stir at room temperature for 6 hours. Water (30 mL) was slowly added and the mixture was extracted with EtOAc and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude residue was purified using flash column chromatograpy on silica gel (20: 1 PE:EtOAc) to provide compound Int-2b (4.2 g, 78%) as a yellow oil. 1H MR (400 MHz, CDC13) delta 7.51-7.53 (m, 1H), 7.20-7.25 (m, 1H), 6.79- 6.81 (m, 1H), 5.85-5.89 (m, 1H), 5.05-5.11 (m, 2H), 4.05-4.11 (m, 2H), 2.47-2.51 (m, 2H).

Statistics shows that 2,4-Difluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 3939-09-1.

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 3939-09-1 as follows. Formula: C7H3F2N

To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added 1,2,4-triazole sodium salt (6.3 g, 70 mmol) and the mixture stirred at 90 0C for 3 h after which the mixture was filtered and the solvent removed. The resulting residue was adsorbed onto silica gel and intermediates 67 and 68 separated by flash chromatography, eluting with 0% to 30% ethyl acetate/hexanes.Intermediate 674-Fluoro-2-(lH-l,2,4-triazol-l-yl)benzonitrile. Colorless needles (2.46 g,18% yield) 1H NMR (500 MHz, CDCl3) delta: 8.89 (IH, s), 8.19 (IH, s), 7.85 (IH, dd, J = 8.7, 5.6 Hz), 7.60 (IH, dd, J= 8.8, 2.4 Hz), 7.28-7.24 (IH, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13. Intermediate e 684-(lH-l,2,4-Triazol-l-yl)-2-fluorobenzonitrile. White solid (0.746 g, 6% yield) 1H NMR (500 MHz, CDCl3) delta: 8.66 (IH, s), 8.15 (IH, s), 7.79 (IH, dd, J= 8.5, 6.7 Hz), 7.69 (IH, dd, J= 9.5, 1.8 Hz), 7.65-7.63 (IH, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13.

According to the analysis of related databases, 3939-09-1, the application of this compound in the production field has become more and more popular.

Reference of 3939-09-1, 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. 3939-09-1, name is 2,4-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Benzyl alcohol (0.77 g, 7.2 mmol) was added to a stirred suspension of potassium tert-butoxide (0.97 g, 8.6 mg) in dioxane (15 ml) at room temperature. After 10 minutes of stirring at room temperature 2,4-difiuorobenzonitrile (1.00 g, 7.2 mmol) was added in one portion. After another 90 minutes water (10 ml) was added and the mixture extracted with diethyl ether (3×10 ml), the combined organic phases were dried using a phase separator and concentrated to solids. The crude material was purified by column (0491) chromatography using silicon dioxide gel, eluting with 25-50% dichloromethane in petroleum ether to afford 2-(benzyloxy)-4-fluorobenzonitrile as a white solid (1.33 g, 81%). (0492) [00317] A cold solution of borane (1.4 ml, 1 M in tetrahydrofuran) was added to 2- (benzyloxy)-4-fluorobenzonitrile (208 mg, 915 mutauetaomicron). After 15 hours of stirring at room temperature additional borane (1.4 ml, 1 M in tetrahydrofuran) was added. After another 19 hours of stirring additional borane (1.0 ml, 1 M in tetrahydrofuran) was added. After 3 hours the mixture was added to sodium hydroxide (5 ml, 1 M aqueous), extracted with ethyl acetate (3×5 ml), the combined organic phases were dried using a phase separator and concentrated afford [2-(benzyloxy)-4-fluorophenyl]methanamine as oil (260 mg, quantitative). This material was used without further purification. (0493) [00318] N-Methyl-4-piperidone (150 mg, 1.32 mmol) was added to a stirred solution of [2-(benzyloxy)-4-fluorophenyl]methanamine (204 mg, 882 mueta omicron) in ethanol (5 ml), after 5 minutes sodium triacetoxyborohydride (372 mg, 1.76 mmol) was added. After 6 hours the reaction mixture was concentrated, redissolved in dichloromethane (5 ml), washed with sodium hydroxide (5 ml, 1 M aqueous), the aqueous phase was extracted with additional dichloromethane (2×1 ml), the combined organic phases were dried using a phase separator, and concentrated to afford the desired intermediate as a yellow oil (253 mg, 87 %).

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

Synthetic Route of 3939-09-1, 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 3939-09-1 as follows.

2,4-Difluorobenzonitrile (2.78 g, 20 mmol) and 3,4,5-trimethoxybenzylamine (3.94 g, 20 mmol) are combined and heated at 140 C for 40 m. The mixture is allowed to cool to RT and is then dissolved in TFA (20 mL) and stirred at RT overnight. The mixture is then concentrated on the rotavap and partitioned between 1N NaOH (enough till basic, ~100 mL) and ethyl acetate (100 mL). The organic layer is removed and the aqueous layer is extracted with more ethyl acetate (100 mL). The combined layers are washed with brine (50 mL), dried (MgSO4) and concentrated to an oil. The mixture is chromatographed (10 to 40%, EtOAc in hexanes) giving the isomers as two well separated products. The later eluding product is concentrated to give 4-Amino-2-fluoro-benzonitrile (1.07 g, 39%) as a white solid. (LC/MS m/z=177.8 for M+H+acetonitrile)

According to the analysis of related databases, 3939-09-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Huang, Kenneth He; Hughes, Philip; Ma, Wei; Ommen, Andy; Woodward, Angela; Veal, James; Barta, Thomas; US2008/76813; (2008); 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. 3939-09-1, name is 2,4-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H3F2N

A mixture of 2, 4-Difluoro-benzonitrile (1.39 g, 10 mmol) , 3- amino-propane-1, 2-diol (0.911 g, 10 mmol) , and ethyl- diisopropyl-amine (1.74 mL) in DMSO (10 itiL) was microwaved at 200 0C for 7 min. Then the reaction mixture was poured into a saturated NH4Cl aq. solution (100 mL) , extracted with EtOAc (3×100 mL) , dried over Na2SCu, filtered, concentrated. The crude mixture was purified by flash silica gel chromatography (EtOAc-Hexane 1:1) to give 2- (2, 3-Dihydroxy-propylamino) -4- fluoro-benzonitrile (0.87 g, 41.4% yield). LCMS (m/z) : M+H = 211.To a mixture of 6, 6-Dimethyl-3-trifluoromethyl-l, 5, 6, 7- tetrahydro-indazol-4-one (0.961 g, 4.14 mmol, 1 eq) and NaH (99 ?ig, 4.14 mmol, 1 eq) in dimethyl acetamide (20 mL) was added slowly 2- (2, 3-Dihydroxy-propylamino) -4-fluoro- benzonitrile (0.87 g, 4.14 mmol, 1 eq) . Then the reaction mixture was stirred at 150 C overnight, cooled, poured into saturated NH4Cl aq. solution (100 mL) , extracted by EtOAc(3×150 mL) , dried over Na2SO4, filtered, concentrated. The crude product was purified by flash silica gel chromatography, eluted by EtOAc to give 2- (2, 3-Dihydroxy-propylamino) -4- (6, 6- dimethyl-4-oxo-3-trifluoromethyl-4 , 5,6, 7-tetrahydro-indazol-l- yl)-benzonitrile (1.7g, 97% yield). LCMS (m/z): M+H = 423. 2- (2, 3-Dihydroxy-propylamino) -4- (6, 6-dimethyl-4-oxo-3- trifluoromethyl-4, 5, 6, 7-tetrahydro-indazol-l-yl) -benzonitrile (1.7 g, 4 mmol, 1 eq) , NaOH (806 mg, 20 mmol, 5 eq) , and H2O2 EPO (3 iriL) were dissolved in EtOH-water (4:1) (40 itiL) . The mixture was microwaved at 120 C for 15 min, then concentrated to dryness, and purified by flash chromatography, eluted by 10% MeOH in EtOAc to give pure 2- (2, 3-Dihydroxy-propylamino) – 4- (6, beta-dimethyl-4-oxo-3-trifluoromethyl-4, 5, 6, 7-tetrahydro- indazol-1-y l)-benzamide (0.52 g, 29% yield). LCMS (m/z) : M+H = 441.

The synthetic route of 3939-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SERENEX, INC.; WO2006/91963; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 3939-09-1, The chemical industry reduces the impact on the environment during synthesis 3939-09-1, name is 2,4-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

To a solution of NaH (1.2 g, 30 mmol) in toluene (50 mL) was added but-3-en-1-ol (1.8 g, 25 mmol) dropwise and the mixture was allowed to stir at room temperature for 30 minutes. 2,4-Difluorobenzonitrile (4.2 g, 30 mmol) was then added in one portion and the mixture was allowed to stir at room temperature for 6 hours. Water (30 mL) was slowly added and the mixture was extracted with EtOAc and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude residue was purified using flash column chromatography on silica gel (20:1 PE:EtOAc) to provide compound Int-2b (4.2 g, 78%) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.51-7.53 (m, 1H), 7.20-7.25 (m, 1H), 6.79-6.81 (m, 1H), 5.85-5.89 (m, 1H), 5.05-5.11 (m, 2H), 4.05-4.11 (m, 2H), 2.47-2.51 (m, 2H).

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

Reference:
Patent; Reger, Thomas S.; Walji, Abbas M.; Sanders, John M.; Wai, John S.; Wang, Liping; US2015/203512; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 3939-09-1,Some common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added the sodium salt of 1,2,4-triazole (6.3 g, 70 mmol) and the mixture was stirred at 90 C. for 3 h, filtered and concentrated. The residue was adsorbed onto Silica gel and purified by flash chromatography eluting with 0%-10%-30% ethylacetate/hexanes to give 4-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile as colorless needles (2.46 g, 18%) and 4-(1H-1,2,4-triazol-1-yl)-2-fluorobenzonitril as a white solid (0.746 g, 6%). 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile. Colorless needles (2.46 g, 18% yield) 1H NMR (500 MHz, CDCl3) delta 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13. 4-(1H-1,2,4-Triazol-1-yl)-2-fluorobenzonitrile. White solid (0.746 g, 6% yield) 1H NMR (500 MHz, CDCl3) delta 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Difluorobenzonitrile, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/111984; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 3939-09-1, The chemical industry reduces the impact on the environment during synthesis 3939-09-1, name is 2,4-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

2,4-Difluorobenzonitrile (50.0 g, 0.359 mol), trans-4-aminocyclohexanol (41.4 g, 0.359 mol, 1 eq.), and N,N-diisopropylethylamine (62.6 mL, 0.359 mol, 1 eq.) were dissolved in 300 mL of DMSO. The reaction vessel was outfitted with a reflux condenser to avoid loss of N,N-diisopropylethylamine. The reaction mixture was then placed in an oil bath that had been pre-heated to 150 C., and was stirred at this temperature for 20 minutes. The solution was then cooled, poured into 750 mL of saturated aqueous NH4Cl, and extracted with ethyl acetate (200 mL¡Á3). The combined organics were washed with brine (150 mL¡Á3), dried over Na2SO4, filtered, and concentrated in vacuo. The resultant residue was purified by column chromatography (1:1 ethyl acetate/hexane) to afford 20.9 g (25% yield) of the desired isomer as a white powder, and 36.1 g (43% yield) of the undesired isomer as a white powder.

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

Reference:
Patent; Huang, Kenneth He; Ommen, Andy J.; Barta, Thomas E.; Hughes, Philip F.; Veal, James; Ma, Wei; Smith, Emilie D.; Woodward, Angela R.; McCall, W. Stephen; US2008/269193; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 3939-09-1, A common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

Example II-2 45 g (0.9 mol) of hydrazine hydrate are added dropwise with stirring to 90 g (0.65 mol) of 2,4-difluorobenzonitrile (cf., for example, EP-A 122,693) in 300 ml of methanol, the mixture is heated at reflux temperature for 3 hours and then concentrated in vacuo, and the residue is stirred with 300 ml of water, filtered off with suction and dried. 73 g (74% of theory) of 4-cyano-3-fluorophenylhydrazine of melting point 136 C. are obtained.

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; Bayer Aktiengesellschaft; US6906006; (2005); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 3939-09-1, 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. 3939-09-1 name is 2,4-Difluorobenzonitrile, 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.

To a mixture of 2,4-difluorobenzonitrile (10.0 g, 72 mmol) and 1,1-dioxo-1?6-[1,2]thiazin-2-ane (8.84 g, 65.4 mmol) in 1:1 tetrahydrofuran/dimethylformamide (40 mL) was added potassium carbonate (9.0 g, 65.4 mmol). The mixture was stirred at 90 C. for 18 h then filtered and concentrated. The residue was purified by flash chromatography (SiO2) eluting with 10%-50% ethyl acetate/hexanes followed by recrystallization from hot ethyl acetate/hexane to give the title compound as white needles (0.537 g, 3% yield). 1H NMR (500 MHz, CD3OD) ? ppm: 7.70 (1H, dd, J=8.8, 5.8 Hz), 7.30 (1H, dd, J=8.8, 2.4 Hz), 7.15-7.12 (1H, m), 3.27 (2H, t, J=5.3 Hz), 3.33 (2H, t, J=6.1 Hz), 2.40-2.35 (2H, m), 2.05-2.01 (2H, m). LCMS (M+H) calcd for C11H16N2OF: 255.06; found: 255.19.

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

Reference:
Patent; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts