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 Preparation of β-Bromoethylphthalimide
  • Preparation of β-Bromoethylphthalimide
  • β-Bromoethylphthalimide could be produced through the following synthetic routes.

    Preparation of β-Bromoethylphthalimide

    In a 1-l. round-bottomed flask are placed 74 g. (0.5 mole) of phthalic anhydride and 30 ml. (0.5 mole) of freshly distilled monoethanolamine. The mixture is heated on a steam bath for 30 minutes; the initial reaction is vigorous. The reaction mixture is cooled to room temperature, and a reflux condenser is attached to the flask. To the cooled reaction mixture is added slowly, with shaking, 32 ml. (91.3 g., 0.34 mole) of freshly distilled phosphorus tribromide. The reaction flask is then placed on a steam bath and heated under reflux with occasional shaking for 1.25 hours. The hot liquid reaction mixture is poured with stirring onto 750 g. of crushed ice. When the ice has melted completely, the crude β-bromoethylphthalimide is collected on a Büchner funnel, washed with cold water, and allowed to dry for a few minutes. The crude product is dissolved in 1.2 l. of aqueous ethanol (50% by volume) with the aid of heat. If necessary a small amount of 95% ethanol is added to effect complete solution. The hot solution is filtered and cooled in a refrigerator. A white crystalline product weighing 94–99 g. is obtained. Concentration of the mother liquor to 400 ml. yields an additional 1–3 g. of product. The total yield of product is 95–102 g. (75–80%); m.p. 80–82°.

    Notice: This preparation should be carried out in a hood.


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