1-Bromoethyl acetate

Pale Yellow Oil

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. 

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.

[1] Patent: CN108383727, 2018, A. Location in patent: Paragraph 0052-0053; 0056-0057; 0061-0062; 0065-0074
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5915 - 5926