Allyl chloride → N-Allylphthalimide

Participants

Reaction Steps

To a stirred mixture of phthalimide potassium salt (20 g, 108 mmol) and tetrabutylammonium bromide (1.04 g, 3.24 mmol, 0.03 equiv) in anhydrous DMF (75 mL) was added allyl chloride (8.84 mL, 108 mmol) at room temperature, and the mixture was stirred at room temperature for 22 h, resulting in a light-yellow suspension. The reaction was quenched by adding cold H2O (150 mL), and the mixture was stirred for 10 min (an ice bath was applied during this time to aid the precipitation). The resulting white suspension was filtered off, washed with H2O (3×50 mL), and air-dried to give N-allylphthalimide (8.5 g, 42% yield) as white solid.

Provenance & Evidence