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A mild and environmentally acceptable synthetic protocol for chemoselective α-bromination of β-keto esters and 1,3-diketones

2006; Elsevier BV; Volume: 47; Issue: 16 Linguagem: Inglês

10.1016/j.tetlet.2006.02.075

1873-3581

Abu T. Khan, Papori Goswami, Lokman H. Choudhury,

Chemical Synthesis and Reactions

A wide variety of unsubstituted β-keto esters can be brominated chemoselectively to the corresponding α-monobromo-β-keto esters by using a combination of vanadium pentoxide, hydrogen peroxide and ammonium bromide in a biphasic system, dichloromethane–water at 0–5 °C. In addition, α-mono substituted β-keto esters, cyclic β-keto-esters and 1,3-diketones can also be brominated selectively using the same protocol.