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6607078 
Journal Article 
Chloramphenicol, II. Synthesis of a-bromo-p-nitroacetophenone 
Chou, PJ 
1960 
8 
(1) 
43-46 
BCI:BCI19603500045413 
Two methods for the preparation of a-bromo-p-nitroacetophenone (VI), a useful intermediate for the synthesis of chloramphenicol, are described. Styrene bromohydrin (II) obtained by the addition of HOB1 to styrene (I) was nitrated to [alpha]-p-nitrophenyl-[beta]-bromoethyl nitrate (III). The nitrate (III) was then hydrolized directly to p-nitrostyrene bromohydrin (V), or preferably through its acetate (IV) by alcoholysis. The bromohydrin (V) was oxidized with chromic acid in acetic acid to give a-bromo-p-nitroacetophenone (VI) in over-all yields of 37.2% and 40.8% respectively. [alpha]-Bromo-p-nitroacetophenone (VI) can also be obtained by nitration of [beta]-bromoethyl benzene (VII) followed by oxidation of the resulting p-nitro compound (VIII) in an over-all yield of 50.8%. || ABSTRACT AUTHORS: Auth. summ