Hydrochloric Acid → N-(4-benzyl-2-iodophenyl)-2-fluoro-4-formylbenzamide

Participants

Reaction Steps

To a slurry of 2-fluoro-4-formylbenzoyl chloride (1.5 mmol) in 5 mL THF was added N-ethyl-N-isopropylpropan-2-amine (0.39 mL, 2.2 mmol) and 4-benzyl-2-iodobenzenamine (0.41 g, 1.3 mmol). After 30 min, the reaction was treated with 1N HCl and Et2O. The organic layer was washed 1×1N HCl, 2×sat'd aq. NaHCO3, and 1× brine. The org. layer was dried over MgSO4, filtered, and concentrated in vacuo. The resulting material was purified by ISCO, 40 g, 0-20% EtOAc/hexanes to give N-(4-benzyl-2-iodophenyl)-2-fluoro-4-formylbenzamide as a white solid. MS (ESI) m/z: Calculated: 459.0; Observed: 457.9 (M−−1).

Provenance & Evidence