1-Bromoethyl acetate

Chemical Properties

Pale Yellow Oil

Uses

1-Bromoethyl Acetate is a 1-haloalkyl ester that is used in the modification of of antibiotics. It is an intermediate that can be usefully used in the preparation of the oral antibiotic Cefuroxime axetil. 

Synthesis

1-bromoethyl acetate is prepared by reacting acetyl bromide and acetaldehyde using zinc chloride as a catalyst. 
After cooling 30 ml of hydrogen bromide / acetic acid (1.2 equiv) to 0 ° C., 53.5 ml (1.0 equiv) of vinyl acetate was slowly added thereto, followed by stirring for 1 hour. It was extracted with dichloromethane, washed with distilled water at 0-5 ° C., dehydrated with anhydrous magnesium sulfate, and distilled under reduced pressure to obtain 81.4 g of 1-bromoethyl acetate.