Water → 1,3-Dimethoxy-5-iodo-2-isopropoxybenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 25.0 g (89.3 mmol) of 4-hydroxy-1-iodo-3,5-dimethoxybenzene in dimethylformamide (125 mL) were added 26.7 mL (267 mmol) of isopropyl iodide and 4.7 g (108 mmol) of a 55 wt. % sodium hydride dispersion in mineral oil. The reaction mixture was stirred at 50° C. for 2.5 hours. With ice cooling, water (125 mL) was added and the mixture was extracted with toluene-hexane (2:1). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield crude crystals. The crude crystals were recrystallized from methanol, whereby 24.0 g of 1-iodo-4-isopropoxy-3,5-dimethoxybenzene was obtained as a colorless crystalline powder (mp: 56.0 to 57.0° C., yield: 83%).

Provenance & Evidence