Potassium Carbonate → Methyl 4-bromo-3-(2-methylallyloxy)benzoate

Participants

Reaction Steps

To a heterogeneous mixture of methyl 4-bromo-3-hydroxybenzoate (1.5 g, 6.49 mmol) and potassium carbonate (1.795 g, 12.98 mmol) in anhydrous acetone (50 mL) was added 3-bromo-2-methylprop-1-ene (2.62 mL, 26.0 mmol) at rt. The mixture was stirred rt for 4 h. The insoluble material was removed by filtration. The filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (100 mL), washed sequentially with 1 N NaOH solution (30 mL), water (2×40 mL), and brine (30 mL). The organic solution was dried over anhydrous MgSO4 and concentrated under vacuum. The residue was applied to ISCO (80 g silica gel, 5-10% ethyl acetate/hexane) to provide the desired product, methyl 4-bromo-3-(2-methylallyloxy)benzoate (1.81 g, 6.35 mmol, 98% yield), as a colorless oil.

Provenance & Evidence