Tetrahedron letters

Unforeseen formation of 2-bromo-3-hydroxybenzaldehyde by bromination of 3-hydroxybenzaldehyde

WAL van Otterlo, JP Michael, MA Fernandes…

Index: Van Otterlo, Willem A. L.; Michael, Joseph P.; Fernandes, Manuel A.; De Koning, Charles B. Tetrahedron Letters, 2004 , vol. 45, # 26 p. 5091 - 5094

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Citation Number: 9

Abstract

Contrary to literature reports, bromination of 3-hydroxybenzaldehyde can afford both 2- bromo-5-hydroxybenzaldehyde and 2-bromo-3-hydroxybenzaldehyde, but 4-bromo-3- hydroxybenzaldehyde was not detected. 2-Bromo-3-hydroxybenzaldehyde was converted into 2-(benzyloxy)-1-bromo-5-methoxy-7-methylnaphthalene. X-ray crystallographic analysis supports the identity of 2-bromo-3-hydroxybenzaldehyde.