4-Hydroxybenzaldehyde → 4-(2-Fluoroethoxy)benzaldehyde

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A mixture of commercially available 4-hydroxybenzaldehyde (2.000 g; 16.40 mmol), 1-fluoro-2-iodoethane (2.849 g; 16.40 mmol), and K2CO3 (4.527 g; 32.80 mmol) in anh. DMF (30 ml) was heated to 70° C., under nitrogen, for 2.5 h. After cooling to rt, the reaction mixture was filtered over a pad of celite. Et2O was added and the organic layer was washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 4-(2-fluoroethoxy)benzaldehyde as a yellow oil. LC-MS (conditions A): tR=0.58 min.; no ionisation.

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