Abstract
A difluoro-derivative of the anti-cancer drug chlorambucil has been made in 7 stages from 4-nitrophenylacetic acid. The acid chloride and ethyl malonate/butyl lithium afforded ethyl 4-(4′-nitrophenyl)-3- oxobutanoate, of which the 3-oxo-function was converted to CF 2 by sulphur tetrafluoride/hydrogen fluoride at room temperature. The nitro-group was reduced to amino, which was alkylated to bis(hydroxy- ethyl) amino using oxirane in acetic acid. Conversion to bis(chloro- ethyl) amino was by carbon tetrachloride/triphenylphosphine. Hydrolysis of the ester group by hydrochloric acid then gave the target product: 4-[4′-bis(2″-chloroethyl) aminophenyl]-3,3-difluorobutanoic acid (3,3-difluorochlorambucil). Other, unsuccessful, approaches were also attempted.
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