[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[N:12][N:13]([CH2:15][C:16]([F:19])([F:18])[F:17])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])(O)=[O:21].[Na+].[O-]S([O-])(=O)=O.[Mg+2].[Mn]([O-])(=O)(=O)=O.[K+].[OH2:37]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:21])[C:9]([C:10]2[CH:11]=[N:12][N:13]([CH2:15][C:16]([F:17])([F:18])[F:19])[CH:14]=2)=[O:37])[CH:5]=[CH:6][CH:7]=1To a solution of 4-[(3-bromophenyl)ethynyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazole (4.90 g, 14.9 mmol) in acetone (150 mL) is added a warm (˜40° C.) solution of NaHCO3 (0.75 g, 8.9 mmol) and MgSO4 (2.70 g, 22.4 mmol) in H2O (150 mL) followed by the addition of solid potassium permanganate (5.2 g, 32.8 mmol) in one portion. After stirring for 40 minutes at room temperature, the reaction mixture is extracted with a solution of Et2O/hexane (1/1) until no product left in aqueous layer. The combined organic extracts is dried (MgSO4) and concentrated to dryness to afford the title compound (4.4 g, 82%) as a solid. mp: 66-67° C. MS (−) ES: 359 (M−H)−.
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