Science of Synthesis

Nelson, S. G., Science of Synthesis, (2007) 20, 47.

Aldehydes can be converted oxidatively into acid bromides. The photochemically mediated reaction of N-bromosuccinimide with aldehydes in the presence of 2,2′-azobisisobutyronitrile as a radical initiator affords the corresponding acid bromides in good yields (78–87%) (‌Scheme 48‌).[‌96‌,‌97‌] Lower reaction yields were obtained from cyclohex-3-ene-1-carbaldehyde, presumably as a result of reactivity of the alkene under the free-radical conditions. A limited number of aliphatic and aromatic aldehydes afford the corresponding esters or amides ‌93‌ by direct functionalization of the intervening acid bromides in fair to good yields (23–84%).

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References

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• 8.Meeeee-Meee, (8888) M 8-8, 888.