Phthalimide → 2-((5-Bromopyridin-3-yl)methyl)isoindoline-1,3-dione

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Reaction Steps

5-Bromo-3-(phthalimidomethyl)pyridine is produced by adding triphenylphosphine (12.1 g, 46.3 mmol) and phthalimide (6.80 g, 46.3 mmol) in dry THF (70 mL) to a stirred suspension of 3-bromo-5-hydroxymethylpyridine (6.70 g, 35.6 mmol), and then adding a solution of diethyl azodicarboxylate (7.30 mL, 46.3 mmol) in dry THF (30 mL) drop-wise. The reaction mixture was stirred at room temperature overnight. After removal of the solvent by rotary evaporation, the crude material was purified by column chromatography to yield 5-bromo-3-(phthalimidomethyl)pyridine (9.5 g, 85% yield).

Provenance & Evidence