BROMINATION OF 2-ACETYL-5-METHYLFURAN

Abstract

The bromination of 2-acetyl-5-methylfuran by bromine and N-bromosuccinimide was studied. The action of N-bromosuccinimide on 5-methyl-2-acetylfuran in various solvents leads to mixtures of an ω-bromo ketone, a 5-bromomethyl derivative, and 5-bromomethyl- ω -bromo ketone. The use of 2,2 ω -azobisisobutyronitrile as activator of the radical process does not make the reaction selective but promotes bromination at the methyl group of the ring. A selective method for the synthesis of 2-(bromoacetyl)-5-methylfuran by the bromination of 2-acetyl-5-methylfuran with bromine was developed.

Authors: N. Saldabol, Yu. Popelis, V. Shatz, and V. Slavinskaya

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (2), pp 161-163

http://link.springer.com/article/10.1007/BF02251701