1-Bromo-2-(chloromethyl)-4,5-dimethoxybenzene → 2-(2-Bromo-4,5-dimethoxy-benzyl)isoindole-1,3-dione

Participants

Reaction Conditions

Reaction Steps

A solution of 1-bromo-2-chloromethyl-4,5-dimethoxy-benzene (26.01 g, 0.09796 mol) in dry DMF (100 mL) was treated with potassium phthalimide (19.05 g, 0.1029 mol). The resulting slurry was heated to 80° C. while stirring under nitrogen for 4.5 h. The resulting mixture was then cooled to room temperature and allowed to stir 16 h. The resulting mixture solidified, was diluted with water (400 mL) and stirred 1 h. The resulting white precipitate was collected via filtration and washed with water (1 L). The white solid was dissolved in boiling methanol (2 L). The resulting solution was reduced to about 1 L, at which time a precipitate began to form. The resulting slurry was allowed to cool to room temperature then placed on an ice bath. The precipitate was collected via filtration to yield 2-(2-bromo-4,5-dimethoxy-benzyl)-isoindole-1,3-dione as a white solid.

Provenance & Evidence