4''-Chloro-5-fluoro-2-hydroxybenzophenone is a metabolite of Progabide (P755350) which is a gamma-aminobutyric acid (GABA) antagonist with antiepileptic activity. 4''-Chloro-5-fluoro-2-hydroxybenzophenone is also used as a reagent in the synthesis of a series of novel dihydrobenzofuranols which displayed antibacterial activity comparable to bacitracin, ciprofloxacin and gentamicin.
Preparation by Fries rearrangement of p-fluorophenyl p-chlorobenzoate,
? with titanium tetrachloride at 150° for 18 h (81%);
? with aluminium chloride, at 130° for 2 h (98%) or at 200° for 5 min or for 15 min (65%).
