Phthalimide → N-(4-Bromopentyl)phthalimide

Participants

Reaction Conditions

Reaction Steps

A one liter, four necked round bottom flask equipped with a mechanical stirrer, thermowatch and condenser was charged with acetone (500 ml), potassium phthalimide (92.5 g, 0.5 moles) and 1,4-dibromopentane (153 g, 0.665 moles). The resulting mixture was refluxed for 24 hours (HPLC showed 2.5% unreacted phthalimide), then cooled to 15° C. Solid sodium bromide was removed by suction filtration and one wash of the cake with acetone (50 ml). The solvent was removed using a rotary evaporator to give 187.2 g of a crude viscous yellow oil. Excess 1,4-dibromopentane (34.5 g) was removed by vacuum distillation at 35-40° C./0.3 mm of pressure, leaving 144.6 g (97.7%) of a yellow viscous oil.

Provenance & Evidence