Journal of fluorine chemistry

Synthesis of 4 [3′-bis (2 ″-chloroethyl) aminophenyl]-4, 4-difluorobutanoic acid [4, 4-difluoro-meta-chlorambucil]

CW Buss, PL Coe, JC Tatlow

Index: Buss, Christopher W.; Coe, Paul L.; Tatlow, John Colin Journal of Fluorine Chemistry, 1997 , vol. 84, # 2 p. 119 - 126

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Citation Number: 2

Abstract

The synthetic sequence to make 4-[4′-bis (2 ″-chloroethyl) aminophenyl]-4, 4- difluorobutanoic acid {4, 4-difluorochlorambucil} was not taken beyond the intermediate stage involving methyl 4, 4-difluoro-4-(4′-aminophenyl) butanoate, since this amine was hydrolytically unstable. Reaction of methyl 4-(3′-nitrophenyl)-4-oxobutanoate with sulfur tetrafluoride, followed by hydrogénation, afforded the stable isomer, methyl 4, 4-difluoro-4- ...