Imidazole → 2-(3-Bromo-2-((tert-butyldimethylsilyl)oxy)propyl)isoindoline-1,3-dione

Participants

Reaction Steps

A solution of 2-(3-bromo-2-hydroxypropyl)isoindoline-1,3-dione (100 mg, 0.352 mmol) in DMF (0.5 mL) was added dropwise to a mixture of DMAP (43.0 mg, 0.352 mmol), imidazole (47.9 mg, 0.704 mmol) and tertbutyldimethylsilyl chloride (74.3 mg, 0.493 mmol) in DMF (1 mL). The mixture was stirred at room temperature for 18 hours. The mixture was diluted with EtOAc (20 ml) and washed with saturated NaHCO3(aq) (20 ml) and brine (3×10 ml). The organic phase was dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-100% EtOAc/hexane, afforded the title compound.

Provenance & Evidence