Phosphonic acid analogs of diclofenac: an Arbuzov reaction of trimethylphosphite with an ortho-quinonoid intermediate

B Mugrage, C Diefenbacher, J Somers, DT Parker…

Index: Mugrage, Ben; Diefenbacher, Clive; Somers, Joe; Parker, David T.; Parker, Tonia Tetrahedron Letters, 2000 , vol. 41, # 13 p. 2047 - 2050

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Citation Number: 8

Abstract

The phosphonic acid analog of the NSAID Diclofenac was efficiently synthesized via an Arbuzov reaction between 2-(2, 6-dichloroanilino) benzyl alcohol and trimethyl phosphite followed by TMSBr promoted dealkylation. Seven related phosphonic acids were synthesized using the same novel acid-catalyzed Arbuzov reaction as the key step.