Tetrahedron Letters

About the reaction of aryl fluorides with sodium sulfide: investigation into the selectivity of substitution of fluorobenzonitriles to yield mercaptobenzonitriles via SN Ar …

T Taldone, PD Patel, HJ Patel, G Chiosis

Index: Taldone, Tony; Patel, Pallav D.; Patel, Hardik J.; Chiosis, Gabriela Tetrahedron Letters, 2012 , vol. 53, # 20 p. 2548 - 2551

Full Text: HTML

Citation Number: 8

Abstract

In this report we describe a simple synthesis of mercaptobenzonitriles from the reaction of fluorobenzonitriles with Na2S in DMF at room temperature and following direct treatment with Zn/HCl. Significantly, 2-and 4-fluorobenzonitriles substituted with chlorine or bromine, but not iodine, undergo selective substitution of fluorine at room temperature to yield synthetically useful halo-substituted mercaptobenzonitriles.