Add time:07/13/2019         Source:sciencedirect.com

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-(3′-aminophenyl)butanoate. Bis(hydroxyethylation) by treatment with oxirane, conversion of OH to Cl by Ph3P/ CCL4, and then hydrolysis of the ester group, gave 4-[3′-bis(2″-chloroethyl)aminophenyl]-4,4-difluorobutanoic acid ,4-difluoro-meta-chlorambucil

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