Phthalimide → 2-(2,2-Dimethoxypropyl)-3-fluoro-4-phthalimidonitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of phthalimide (4.4 g; 30 mmol) in anhydrous DMF (40 ml) cooled to 0° C. was added sodium hydride (1.29 g, 32 mmol, 60% in oil). The mixture was stirred at this temperature for 30 minutes before the addition of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (6 g, 23 mmol), (prepared as described for the starting material in Example 11). The reaction mixture was heated at 100° C. for 3 hours under argon. Upon cooling to ambient temperature, the reaction mixture was poured over ice/water (200 ml) and the formed precipitate was collected by filtration and washed with water and ether. The solid was purified by flash chromatography using methylene chloride/methanol (99/1). Evaporation of the solvent gave 2-(2,2-dimethoxypropyl)-3-fluoro-4-phthalimidonitrobenzene (5.6 g, 63%) as a yellow solid.

Provenance & Evidence