Category: 185147-07-3

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. 185147-07-3, name is 2-Fluoro-3-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-Fluoro-3-methylbenzonitrile

To a mixture of 2-fluoro-3-methylbenzonitrile (4.0 g, 29.6 mmol) and 2H-1 ,2,3- triazole (2.04 g, 29.6 mmol) in DMF (80 ml_) was added potassium carbonate (8.26 g, 59.2 mmol). The resulting mixture was heated to 120 C for 2h. The mixture was cooled, diluted with water and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (S1O2, ethyl acetate/hexanes, gradient 0-50%) to yield the title compound (1 .5 g, 26%). MS (ESI) mass calcd. for Ci0H8N4,184.2; m/z found, 185.1 [M+H]+. 1H NMR (500 MHz, CDCI3): 7.95 (s, 2H), 7.66 (d, J = 7.7, 0.7 Hz, 1 H), 7.59 (d, J = 7.8, 0.6 Hz, 1 H), 7.50 (dd, J = 9.8, 5.7 Hz, 1 H), 2.20 (s, 3H).; Intermediate 36: 3-Methyl-2-(1 H-1 ,2,3-triazol-1 -yl)benzonitrile.The title compound was a byproduct of the synthesis of Intermediate 35 (3.1 g, 56%). MS (ESI) mass calcd. for CioH8N4, 184.2; m/z found, 185.1 [M+H]+. 1 H NMR (500 MHz, CDCI3): 7.94 (d, J = 2.1 Hz, 1 H), 7.87 (d, J = 1 .1 Hz, 1 H), 7.71 – 7.67 (m, 1 H), 7.67 – 7.62 (m, 1 H), 7.56 (dd, J = 9.7, 5.8 Hz, 1 H), 2.17 (s, 3H).

The synthetic route of 185147-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 185147-07-3,Some common heterocyclic compound, 185147-07-3, name is 2-Fluoro-3-methylbenzonitrile, molecular formula is C8H6FN, 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.

2-fluoro-3-methylbenzonitrile (18 g, 133 mmol) was added to a solution of potassium nitrate (13.5 g, 133 mmol) in sulfuric acid (250 mL) cooled at 0C, the mixture was allowed to stir at room temperature for 40 minutes. The reaction mixture was poured into ice water and the pale yellow precipitate was filtered off and dried in the vacuum oven yielding crude 2-fluoro-3- methyl-5-nitro-benzonitrile (18 g). Crude 2-fluoro-3-methyl-5-nitro-benzonitrile (18 g) was stirred in MeOH (210 mL) and water (70 mL). Fe powder (16.7 g) and HC1 (36 mL, 5 equiv) were added and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then filtered through celite and after removal of organic solvent, the mixture was adjusted to pH 9 with saturated solution of sodium carbonate and extracted with CH2C12 twice. The combined organic layers were dried over sodium sulfate and evaporated to dryness to provide a yellow oil. The crude product was purified by column chromatography to provide 5-amino-2- fluoro-3-methyl-benzonitrile (5.1 g) as a pale yellow solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-3-methylbenzonitrile, its application will become more common.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2014/184365; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

185147-07-3, name is 2-Fluoro-3-methylbenzonitrile, 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. COA of Formula: C8H6FN

Step 1 K2CO3 (8.18 g, 59.2 mmol) was added to a RT solution of 2-fluoro-3-methylbenzonitrile (4.0 g, 29.6 mmol) and 1H-1,2,3-triazole (1.72 mL, 29.6 mmol) in DMF (80 mL) and the resulting suspension was heated to 120 C. for 4 h. The reaction mixture was cooled to RT and quenched with water before being extracted with EtOAc (3*). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by flash chromatography (eluting with a gradient of 33% to 50% EtOAc in hexane) to give 3-methyl-2-(2H-1,2,3-triazol-2-yl)benzonitrile as a white solid. LC-MS B: tR=0.62 min; [M+H]+=185.16.

The synthetic route of 185147-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; Bolli, Martin; Boss, Christoph; Brotschi, Christine; Heidmann, Bibia; Sifferlen, Thierry; Williams, Jodi T.; US2015/158855; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 185147-07-3, These common heterocyclic compound, 185147-07-3, name is 2-Fluoro-3-methylbenzonitrile, 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.

Intermediate 81 : 3-Methyl-2-(2H-1 ,2,3-triazol-2-yl)benzonitrile.To a mixture of 2-fluoro-3-methylbenzonitrile (4.0 g, 29.6 mmol) and 2H-1 ,2,3- triazole (2.04 g, 29.6 mmol) in DMF (80 mL) was added potassium carbonate (8.26 g, 59.2 mmol). The resulting mixture was heated to 120 C for 2h. The mixture was cooled, diluted with water and extracted with EtOAc. The organic layers were combined, dried over Na2S04, filtered and concentrated. The residue was purified by FCC (Si02, ethyl acetate/hexanes, gradient 0-50%) to yield the title compound (1 .5 g, 26%). MS (ESI) mass calcd. for Ci0H8N4, 184.2; m/z found, 185.1 [M+H]+. 1H NMR (500 MHz, CDCI3): 7.95 (s, 2H), 7.66 (d, J = 7.7, 0.7 Hz, 1 H), 7.59 (d, J = 7.8, 0.6 Hz, 1 H), 7.50 (dd, J = 9.8, 5.7 Hz, 1 H), 2.20 (s, 3H).

The synthetic route of 185147-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 185147-07-3, name is 2-Fluoro-3-methylbenzonitrile, molecular formula is C8H6FN, 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. name: 2-Fluoro-3-methylbenzonitrile

Intermediate 20: 3-Methyl-2-(2H-1 ,2,3-triazol-2-yl)benzonitrile.To a mixture of 2-fluoro-3-methylbenzonitrile (4.0 g, 29.6 mmol) and 2H-1 ,2,3- triazole (2.04 g, 29.6 mmol) in DMF (80 mL) was added potassium carbonate (8.26 g, 59.2 mmol). The resulting mixture was heated to 120 C for 2h. The mixture was cooled, diluted with water and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (S1O2, ethyl acetate/hexanes, gradient 0-50%) to yield the title compound (1 .5 g, 26%). MS (ESI) mass calcd. for Ci0H8N4,184.2; m/z found, 185.1 [M+H]+. 1 H NMR (500 MHz, CDCI3): 7.95 (s, 2H), 7.66 (d, J = 7.7, 0.7 Hz, 1 H), 7.59 (d, J = 7.8, 0.6 Hz, 1 H), 7.50 (dd, J = 9.8, 5.7 Hz, 1 H), 2.20 (s, 3H).Intermediate 21 : 3-Methyl-2-(1 H-1 ,2,3-triazol-1 -yl)benzonitrile.The title compound was also a product of the synthesis of Intermediate 20 (3.1 g, 56%). MS (ESI) mass calcd. for CioH8N4, 184.2; m/z found, 185.1 [M+H]+. 1 H NMR (500 MHz, CDCI3) : 7.94 (d, J = 2.1 Hz, 1 H), 7.87 (d, J = 1 .1 Hz, 1 H), 7.71 – 7.67 (m, 1 H), 7.67 – 7.62 (m, 1 H), 7.56 (dd, J = 9.7, 5.8 Hz, 1 H), 2.17 (s 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 185147-07-3, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts