Anodic monofluorination at the position α to the oxygen atom of the (E)-3-benzylidene-2,3-dihydrochroman-4-one derivatives was successfully carried out to provide the corresponding 2-fluorochromanones selectively. This is the first regioselective electrochemical fluorination of fused-type,oxygen-containing heterocyclic compounds. Anodic fluorination of a chromone derivative also gavea similar fluorinated chromanone stereoselectively.