Iodine → Benzhydrol

Participants

Reaction Steps

To a dry flask equipped with a condenser, an addition funnel, and a magnetic stirrer were added magnesium turnings (2.5 mmol), THF (0.5 mL), and a small piece of iodine. To this was added via the addition funnel approximately ⅓ of 3,4,5-trimethoxybromobenzene (2.5 mmol) in 1.3 mL of THF. When the solution became colorless (heating may be needed), the remaining 3,4,5-trimethoxybromobenzene solution was added dropwise to the solution under mild refluxing. Stirring was then continued for 1 h at room temperature. The resulting solution was then slowly added to 6-methoxybenzofuran-3-carbaldehyde (0.100 g, 0.176 mmol) in anhydrous THF (5 mL) at 0° C. After the addition, the solution was allowed to stir at room temperature for another 20 min. Then, a saturated NH4Cl solution (5 mL) was slowly added at 0° C., and the mixture was stirred for 10 min. The aqueous layer was separated and extracted with Et2O (3×10 mL). The combined organic layers were washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography to provide benzhydrol (0.097 g, 50%).

Provenance & Evidence