A. Sinhababu, R. Borchardt
Jun 1, 1983
Citations
0
Influential Citations
9
Citations
Journal
Journal of Organic Chemistry
Abstract
A general method for the onestep conversion of bromobenzaldehydes to the corresponding hydroxybenzaldehydes has been developed. The method involves in situ protection of the aldehyde function of the bromobenzaldehyde as ita lithium morpholinoalkoxide, followed by lithium-bromine exchange, reaction with nitrobenzene at -75 “C, and a subsequent acidic workup. The method has been applied to the synthesis of 4,5-dimethoxy-3-hydroxy(la), 3,5-dimethoxy-2-hydroxy(2a), 3,5-bis(benzyloxy)-2-hydroxy(2b), 3,4-dimethoxy-2-hydroxy(14), 3hydroxy-4,5-(methylenedioxy)(16), and 4,5-dimethoxy-2-hydroxybenzaldehydea (18) from the bromobenzaldehydes 4, 12a, 12b, 13, 15, and 17, respectively.