An efficacious method for the halogenation of β-dicarbonyl compounds under mildly acidic conditions

• Published in: Tetrahedron letters Vol. 46; no. 28; pp. 4749 - 4751
• Main Authors: Meketa, Matthew L., Mahajan, Yogesh R., Weinreb, Steven M.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 11.07.2005; Elsevier
• Subjects: 1,3-Diketones; Bromination; Chemistry; Chemistry, Organic; Chlorination; Malonates; Physical Sciences; Science & Technology; Vinyl chlorides; β-Ketoesters; Chlorination; 1,3-Diketones; β-Ketoesters; Bromination; Malonates; Vinyl chlorides; CONVENIENT SYNTHESIS; HALIDES; beta-ketoesters; malonates; KETO-ESTERS; REGIOSPECIFIC SYNTHESIS; RADICAL CYCLIZATION; vinyl chlorides; AGENTS; 1,3-diketones; chlorination; bromination
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2005.05.055

A variety of 1,3-diketones, β-ketoesters and malonates can be chlorinated in high yields using sodium hypochlorite in a 5:2 mixture of acetone/acetic acid at 0 °C for 1 h. Similarly, bromination of these dicarbonyl substrates can be accomplished under the same conditions using sodium hypobromite. A variety of 1,3-diketones, β-ketoesters and malonates can be chlorinated in high yields using sodium hypochlorite in a 5:2 mixture of acetone/acetic acid at 0 °C for 1 h. Similarly, bromination of these dicarbonyl substrates can be accomplished under the same conditions using sodium hypobromite.