3-Chloro-4-fluorophenol → 3-(3-Chloro-4-fluorophenoxy)-2-hydroxy-2-methyl-N-(2-methyl-3-nitro-phenyl)propionamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:10][C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][C:12]=1[NH:20][C:21]([C:23]1([CH3:26])[CH2:25][O:24]1)=[O:22]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][CH2:26][C:23]([OH:24])([CH3:25])[C:21]([NH:20][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([N+:17]([O-:19])=[O:18])[C:11]=1[CH3:10])=[O:22]Participants
3
Procedure
3-(3-Chloro-4-fluorophenoxy)-2-hydroxy-2-methyl-N-(2-methyl-3-nitrophenyl)propionamide was prepared as described in Example 1 starting from 3-chloro-4-fluorophenol and 2-methyloxirane-2-carboxylic acid (2-methyl-3-nitrophenyl)amide. The crude product was purified by flash chromatography (dichloromethane-1% methanol). 1H NMR (400 MHz, DMSO-d6): 1.44 (3H, s), 2.27 (3H, s), 3.99 (1H, d, J=9.8 Hz), 4.23 (1H, d, J=9.8 Hz), 6.15 (1H, s), 6.92-6.97 (1H, m), 7.17-7.20 (1H, m), 7.29-7.35 (1H, m), 7.41-7.46 (1H, m), 7.66-7.69 (1H, m), 7.72-7.75 (1H, m), 9.72 (1H, s).