[F:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].I[CH2:12][CH3:13].C([O-])([O-])=O.[K+].[K+].CCOCC>CN(C=O)C>[CH2:12]([O:10][C:3]1[C:2]([F:1])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6])[CH3:13]A mixture of commercially available 3-fluoro-2-hydroxybenzaldehyde (5.000 g; 35.70 mmol), iodoethane (11.131 g; 71.40 mmol), and K2CO3 (5.918 g; 42.80 mmol) in anh. DMF (100 ml) was heated to 80° C., under nitrogen, for 3 h. Et2O was added and the organic layer was washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 2-ethoxy-3-fluorobenzaldehyde as a yellow oil. LC-MS (conditions A): tR=0.74 min.; no ionisation.
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