1,4-Benzodioxan → Methanone, (2-bromo-5-iodophenyl)(2,3-dihydro-1,4-benzodioxin-6-yl)-

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Reaction Steps

To a stirred solution of 2-bromo-5-iodo-benzoyl chloride (−158 g, 457 mmol) in DCM (1500 ml) was added benzo(1,4)-dioxane (65.8 ml, 549 mmol) at 0° C. To this reaction mixture, aluminum chloride (195.4 g, 1465 mmol) was added in portions. After stirring for overnight at room temperature, reaction mixture was poured into crushed ice. This was extracted with dichloromethane (1000 ml×2). Dichloromethane layer was washed with water (1000 ml), saturated aqueous sodium bicarbonate solution (1000 ml×2), brine (1000 ml), dried over sodium sulfate, and concentrated. The solid product was triturated with hexanes. The product was dried under vacuum to give 180 g of (2-bromo-5-iodo-phenyl)-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone.

Provenance & Evidence