Benzyl Bromide → 5-Benzyloxy-4-t-butylbenzofuran

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Reaction Steps

In 200 ml of N,N-dimethylformamide were dissolved 40.0 g of 4-t-butyl-5-hydroxybenzofuran [J. Org. Chem. 53, 4135 (1988)], 43.0 g of benzyl bromide and 28.8 g of potassium carbonate, and the mixture was stirred at room temperature for a whole day and night. After N,N-dimethylformamide was distilled off under reduced pressure, the solution was combined with water and extracted with ethyl acetate. The extracted layers were washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 10% ethyl acetate) to give 49.1 g of 5-benzyloxy-4-t-butylbenzofuran as a colorless oil (yield 83%).

Provenance & Evidence