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Oc-Bromination of Ketones and Dehydrobromination a-Bromination of ketones proceeds via the acid catalyzed formation of the enol. The enol is attacked by bromine, and finally, a proton is lost giving the product. Acetic acid is a convenient medium for the reaction since it is a proton source as well as an excellent solvent for the reagents. Examples (77) of the bromine-acetic acid system are given below. 50 6. THE INTRODUCTION OF HALOGEN R-C-CH2-R' O Br R—C—CH-R' 4- Br e -H+ R—C—CH- R' Il O Base catalyzed dehydrobromination of a-bromoketones is frequently employed in steroidal systems as a means to obtain

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Advanced Organic Synthesis, Methods and Techniques by Richard S. Monson

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