反应详情

1-chloro-4-iodo-2-(4-methoxybenzyl)benzene (10.0 g, 27.9 mmol) was dissolved in methylene chloride (150 mL). To the resulting mixture was added dropwise boron tribromide (21 g, 83.7 mmol) under cooling in an ice-water bath. After the completion of dropwise addition, the mixture was warmed up to room temperature, and stirred for 3 hr. The mixture was quenched with a saturated sodium bicarbonate solution, was separated into an aqueous phase and an organic phase. The aqueous phase was extracted with methylene chloride (150 mL×2). The organic phases were combined, washed with a saturated sodium chloride solution, dried over anhydrous sodium sulphate, and concentrated under a reduced pressure. The resulting crude product was purified with a silica-gel column chromatography (ethyl acetate:petroleum ether=0-1:20) to produce 8.5 g of a product in a yield of 88%.

1. temperatureunder cooling in an ice-water bath
2. additionAfter the completion of dropwise addition
3. customThe mixture was quenched with a saturated sodium bicarbonate solution
4. customwas separated into an aqueous phase
5. extractionThe aqueous phase was extracted with methylene chloride (150 mL×2)
6. washwashed with a saturated sodium chloride solution
7. dry with materialdried over anhydrous sodium sulphate
8. concentrationconcentrated under a reduced pressure
9. customThe resulting crude product was purified with a silica-gel column chromatography (ethyl acetate:petroleum ether=0-1:20)