Synthesis of 4-[4′-bis(2″-chloroethyl)aminophenyl]-3,3,4,4-tetrafluorobutanoic acid [3,3,4,4-tetrafluorochlorambucil]

Add time:07/12/2019    Source:sciencedirect.com

Reaction of 2,2-dichloro-2-(4′-nitrophenyl)acetonitrile with mercury(II) oxide/pyridinium poly (hydrogen fluoride), (aqueous work-up), gave 2,2-difluoro-2-(4′-nitrophenyl)acetamide, from which were made the parent acid and thence its acid chloride. This and ethyl propanedioate/methyl lithium afforded ethyl 4,4-difluoro-4-(4′-nitrophenyl)-3-oxobutanoate, converted by SF4/HF into ethyl 3,3,4,4-tetrafluoro-4-(4′-nitrophenyl)butanoate. Catalytic hydrogenation of the nitro-group then gave the 4′-amine, which was bis (hydroxyethylated) using oxirane. Conversion to the bis(chloroethyl) analogue utilized Ph3P/CCl4, whence acidic hydrolysis afforded 4[4′-bist 2″-chloroethyl) aminophenyl ]-3,3,4,4-tetrafluorobutanoic acid.

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