HCID 20085919, compound → HCID 20085916, compound

Participants

Reaction Steps

A solution of 5-bromo-2-(4-bromophenoxymethyl)benzoic acid (100 g, 0.26 mole), and trifluoroacetic anhydride (160 mL) in one liter of methylene chloride containing 20 drops of boron trifluoride-ether complex was refluxed for three hours. The mixture was poured into ice water and then extracted with diethyl ether. Concentration of ether solution under reduced pressure and chromatography of the residue on a silica gel column (Waters Associates, Prep 500) with hexane/ethyl acetate (9:1) gave the ketone (45 g) mp 193°-194° C. pmr (DMSO-d6) δ: 8.12 (d, J=2.7 Hz, 1H, H4) , 7.27-7.91 (m, 4H, aromatic H) , 7.10 (d, J=8.8 Hz, 1H, H4), 5.32 (s, 2H, ArCH2O).

Provenance & Evidence