Nonselective bromination-selective debromination strategy: selective bromination of unsymmetrical ketones on singly activated carbon against doubly activated carbon

Han Young Choi; Dae Yoon Chi

doi:10.1021/ol0271638

Nonselective bromination-selective debromination strategy: selective bromination of unsymmetrical ketones on singly activated carbon against doubly activated carbon

Org Lett. 2003 Feb 20;5(4):411-4. doi: 10.1021/ol0271638.

Authors

Han Young Choi¹, Dae Yoon Chi

Affiliation

¹ Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon 402-751, Korea.

PMID: 12583731
DOI: 10.1021/ol0271638

Abstract

[reaction: see text] We have found a new synthetic method for the preparation of the alpha-bromoketones that are brominated in the less activated terminal position of unsymmetrical ketones. Brominations in short reaction times (kinetically controlled) provided internally brominated compounds as a major product. However, brominations in longer reaction times (thermodynamically controlled) gave more of the terminally brominated compound through the reversible reaction by Br(2) and produced hydrogen bromide. Several brominated compounds at the terminal position were successfully prepared through the new synthetic route.