Dichloromethane → HCID 67411503, compound

Participants

Reaction Steps

The mixture of (R)-4-(6-Hydroxy-naphthalen-2-yl)-4-methyl-oxazolidin-2-one (221.7 mg, 0.0009114 mol), N-iodosuccinimide (226 mg, 0.00100 mol) and zirconium tetrachloride (33 mg, 0.00014 mol) in methylene chloride (16 mL, 0.25 mol) was stirred at room temperature for 3 h. After filtrating through Celite and washing with methylene chloride, the concentrated residue was chromatographed to give (R)-4-(6-hydroxy-5-iodonaphthalen-2-yl)-4-methyloxazolidin-2-one as a light yellow solid (290 mg, 86%). LCMS: Rf=1.33 min (370.07, M+1, 100%), 1H NMR (400 MHz, MeOD) δ=8.10 (d, J=8.9 Hz, 1 H), 7.79 (s, 1 H), 7.77 (d, J=8.8 Hz, 1 H), 7.56 (dd, J=2.1, 8.9 Hz, 1 H), 7.18 (d, J=8.8 Hz, 1 H), 4.52 (d, J=8.5 Hz, 1 H), 4.43 (d, J=8.5 Hz, 1 H), 1.80 (s, 3 H).

Provenance & Evidence