An improved preparation and use of 2-bromoacetoacetaldehyde in a new synthesis of 2-substituted-4-acetylimidazoles

CA Lipinski, TE Blizniak, RH Craig

Index: Lipinski, Christopher A.; Blizniak, Thaddeus E.; Craig, Rebecca H. Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 566 - 570

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Citation Number: 17

Abstract

Sodium acetoacetaldehyde was prepared by formylation of acetone with ethyl formate, using sodium ethoxide in ether. A major impurity always present in our sodium acetoacetaldehyde was 10-40 mol% sodium formate, which was easily deteded by NMR and was also confirmed by IR analysis. The presence of sodium formate as a contaminant leads to the generation of hydrogen bromide due to oxidation of sodium formate by bromine (eq l). 6