Tetrahedron

A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes

JK Augustine, YA Naik, AB Mandal, N Chowdappa…

Index: Augustine, John Kallikat; Naik, Y. Arthoba; Mandal, Ashis Baran; Chowdappa, Nagaraja; Praveen, Vinuthan B. Tetrahedron, 2008 , vol. 64, # 4 p. 688 - 695

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Citation Number: 8

Abstract

Hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group to corresponding aldehydes without affecting the ester group was successfully accomplished in high yields by subjecting them to refluxing pyridine. Both aromatic and heteroaromatic substrates gave the corresponding aldehydes in good yields. This method was efficiently adapted for the large scale synthesis of 2d and 2f.