Butofilolol

Butofilolol (trade name Cafide) is a beta-blocker drug for the treatment of essential hypertension (high blood pressure). It is not known to be marketed anywhere.

It is an example of a butyrophenone.

Synthesis

 * Butofilolol synthesis.svg

The Fries rearrangement of the ester formed by 4-fluorophenol (1) and butryryl chloride (2) gives 5'-fluoro-2'-hydroxybutyrophenone (3). Treatment with epichlorohydrin in the presence of base leads to 1-[5-fluoro-2-(oxiranylmethoxy)phenyl]butan-1-one (4). Lastly, reaction with tert-butylamine gives butofilolol.