New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 1157938-97-0, name is 1-(2,5-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H7F2N3O
Propionitrile (11 g, 0.200 mmol) was dissolved in 100 mL of anhydrous THF.Replace with nitrogen three times and slowly add at -78CBistrimethylsilyllithium200 mL (1M) of tetrahydrofuran solution, stir for 10 min, then add magnesium bromide (46 g, 0.25 mmol),After stirring for 20 min, 1-(2,5-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (22.3 g, 0.100 mmol) was added and slowly raised. To -50 C, then the solution is stirred for 2 hours,Until the disappearance of the raw material, 100 mL saturated ammonium chloride solution and 150 mL ethyl acetate were added.Extract twice, combine the organic phases, and wash three times with saturated saline solution.The organic phase was dried, spin-dried and passed through a column of silica gel (PE:EA=1:2) according to formula (I)23.6 g (yield: 84.9%, d.e. >99%) of de(2S,3R) and (2R,3S) white solids were mixed.The resulting solid was dissolved in 50 ml toluene, 100 ml methyl tert-butyl ether andIn a mixed solvent of 20 mL of methanol, D-10-camphorsulfonic acid (19.7 g, 84.91 mmol) was added.Heat the reaction to 60 C, react for 1h, slowly cool and cool, filter,Obtain a white solid, then add water, stir with sodium bicarbonate, extract with dichloromethane,The organic phase was concentrated to obtain the diastereoisomer of (2S,3R) 8.49 g according to formula (I)(Yield: 35.9%, e.e. >99%, d.e. >99%) LC-MS of the resulting compoundThe result of H-NMR measurement is the same as that described in Example 2.
If you are hungry for even more, make sure to check my other article about 1157938-97-0, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Liu Meijun; (18 pag.)CN106317044; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics