Category: 447-60-9

Electric Literature of 447-60-9, 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 447-60-9 as follows.

To a solution of 2,2,6,6-tetramethylpiperidine (0.99 g, 7.02 mmol) in THF (25 ml) was added n-BuLi (2.80 ml, 2.5 M hexane solution, 7.02 mmol) at -10 C. After stirring for 10 min, this solution was cooled to -78 C., tris(1-methylethyl)borate (1.58 g, 8.4 mmol) was added, and the mixture was stirred for 5 min. To this solution was added a solution of 2-(trifluoromethyl)benzonitrile (1.00 g, 5.85 mmol) in THF (10 ml), and the mixture was stirred at -78 C. for 2 hr. The reaction solution was allowed to warm to room temperature, the reaction was quenched with acetic acid, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, the precipitated solid was filtered off, and the filtrate was concentrated to give the title compound (3.14 g) as a mixture. This was used for the next reaction without performing further purification and identification.

According to the analysis of related databases, 447-60-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kasai, Shizuo; Kamaura, Masahiro; Cho, Nobuo; US2011/251187; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 447-60-9,Some common heterocyclic compound, 447-60-9, name is 2-(Trifluoromethyl)benzonitrile, molecular formula is C8H4F3N, 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.

45.3 ml of a 1.8 M lithium diisopropylamide THF solution (81.6 mmol) was diluted with 68 ml of THF. Thereafter, 28 ml of a THF solution containing 5.0 g (27.2 mmol) of the 5-chloro-2,N-dimethylbenzamide prepared in Step A was added dropwise to the diluted solution at -78C. Thereafter, 28 ml of a THF solution containing 4.65 g (27.2 mmol) of 2-trifluoromethylbenzonitrile was further added thereto, and the obtained mixture was then stirred at -78C for 2.5 hours. The temperature of the reaction solution was increased to a room temperature, and a saturated ammonium chloride aqueous solution was added thereto, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and was then dried over anhydrous sodium sulfate. Thereafter, a solid generated as a result of vacuum concentration was filtrated, so as to obtain 6.87 g (78%) of 7-chloro-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one in the form of a colorless solid. 1H-NMR (270MHz, CDCl3) delta (ppm): 6.49 (1H, s), 7.33-7.72 (5H, m), 7.81-7.84 (1H, d, J=7.26Hz), 8.32-8.33 (1H, d, J=1.65Hz), 9.18 (1H, brs) ESI (LC-MS positive mode) m/z 324 (M+H).

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

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1724262; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 447-60-9, These common heterocyclic compound, 447-60-9, name is 2-(Trifluoromethyl)benzonitrile, 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.

General procedure: The mixture of 1-ferrocenyl-2-methylpropan-1-ol (1) (645 mg, 2.5 mmol) and the nitrile 2 (2.5 or 3.0 mmol) in DCE(5 mL) was added dropwise with vigorous stirring to MsOH (1.30 mL, 20 mmol) at room temperature. The resulting mixture was then heated with stirring at 60 C for the noted reaction time. After, the reaction mixture was cooled to roomtemperature, poured into a mixture of crushed ice (20 g) and 25% aq NH3 (6 mL) and extracted with EtOAc (80 mL × 3). The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification of the crude mixture by silica gel column chromatography gave the desired product 3

Statistics shows that 2-(Trifluoromethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 447-60-9.

Reference:
Article; Rozhkova, Yuliya S.; Plekhanova, Irina V.; Gorbunov, Alexey A.; Stryapunina, Olga G.; Chulakov, Evgeny N.; Krasnov, Victor P.; Ezhikova, Marina A.; Kodess, Mikhail I.; Slepukhin, Pavel A.; Shklyaev, Yurii V.; Tetrahedron Letters; vol. 60; 11; (2019); p. 768 – 772;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 447-60-9, 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 447-60-9 as follows.

Step B 7-Chloro-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one; [Show Image] A 1.8 M lithium diisopropylamide THF solution (45.3 ml, 81.6 mmol) was diluted with THF (68 ml). Thereafter, a solution obtained by dissolving the 5-chloro-2,N-dimethylbenzamide (5.0 g, 27.2 mmol) prepared in step A in THF (28 ml) was added dropwise to the diluted solution at -78C. Thereafter, a solution obtained by dissolving 2-trifluoromethylbenzonitrile (4.65 g, 27.2 mmol) in THF (28 ml) was further added thereto, and the obtained mixture was then stirred at -78C for 2.5 hours. The temperature of the reaction solution was increased to a room temperature, and a saturated ammonium chloride aqueous solution was added thereto, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and was then dried over anhydrous sodium sulfate. Thereafter, a solid generated as a result of vacuum concentration was filtrated, so as to obtain 7-chloro-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (6.87 g; yield: 78%) in the form of a colorless solid. 1H-NMR (270MHz, CDCl3) delta (ppm): 6.49 (1H, s), 7.33-7.72 (5H, m), 7.81-7.84 (1H, d, J=7.26Hz), 8.32-8.33 (1H, d, J=1.65Hz), 9.18 (1H, brs) ESI (LC-MS positive mode) m/z 324 (M+H).

According to the analysis of related databases, 447-60-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1854792; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts