Syntheses of 1-(p-Nitrophenyl)-3-(2, 2-dichloroacetamido)-1, 2-propanediols

2-Bromo-3-acetoxyropiophenone (VI) was reacted with potassium phthalimide in dimethylformamide to give 2-acetoxy-3-phthalimidopropiophenone (XI). XI was submitted to hydrogenation over palladium on charcoal followed by acetylation with acetic anhydride and pyridine to yield two DL-isomers of 1-phenyl-3-phthalimide-1, 2-propanediol diacetate (XIII). Two DL-isomers of 1-(p-nitrophenyl)-3-(2, 2-dichloroacetamido)-1, 2-propanediol (I), the position isomers of chloramphenicol, were derived from XIII.