1,3-Difluorobenzene → HCID 10813782、化合物

反応式

[F:1][C:2]([F:25])([CH:22]([F:24])[F:23])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[N:14]([C@H:17]([CH3:21])[C:18](Cl)=[O:19])[N:13]=[CH:12]2)=[CH:7][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1>ClCCl>[F:30][C:31]1[CH:32]=[C:33]([F:37])[CH:34]=[CH:35][C:36]=1[C:18](=[O:19])[C@H:17]([N:14]1[C:15](=[O:16])[N:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][C:2]([F:25])([F:1])[CH:22]([F:24])[F:23])=[CH:6][CH:7]=2)[CH:12]=[N:13]1)[CH3:21]

参加物

実験手順

(2R)-2-[4-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]propanoyl chloride (1 g) was dissolved in 20 ml of dichloromethane, to which 2.5 ml of 1,3-difluorobenzene and 1.50 g of anhydrous aluminium chloride in a powdery form were added. The mixture was refluxed with heating for eight hours. After cooling, the reaction solution was poured into 50 ml of ice water and extracted from a mixture of 100 ml of ethyl acetate and 50 ml of diisopropyl ether. The extract was washed with 30 ml of 1N-hydrochloric acid and 30 ml of a saturated aqueous solution of sodium chloride successively, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 60 g, eluent; hexane:ethyl acetate:acetic acid=2:1:0.03) to give 0.77 g of 2-[(1R)-2-(2,4-difluorophenyl)-2-oxo-1-methylethyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (yield: 61%) as a pale yellow oil.