[Hydroxy(tosyloxy)iodo]benzene → HCID 86665799, compound

Participants

Reaction Steps

The compound was produced with reference to the method described in the literature (Synth. Commun., 1994, 24 (18), 2637). A solution of 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate (RE6) (15.0 g, 43 mmol), [hydroxy(tosyloxy)iodo]benzene (20.4 g, 52 mmol) and p-toluenesulfonic acid monohydrate (375 mg) in acetonitrile (750 mL) was stirred at 50° C. for 16 hours. The solvent was distilled off under reduced pressure. Ethyl acetate (500 mL) was added to the obtained concentrated residue, and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine in this order and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained concentrated residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→1:2) to obtain the title compound (RE7) (4.92 g, 33%) as a pale yellow solid.

Provenance & Evidence