Sodium Iodide → 4-(Iodomethyl)-1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octane

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Reaction Conditions

Reaction Steps

A mixture of (1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate (1G; 950 mg, 2.05 mmol) and NaI (3.07 g, 20.45 mmol) in MeCN (10 mL) was heated to 70° C. for 72 h. The reaction mixture was cooled to rt, filtered and concentrated in vacuo. The residual crude product was purified by flash chromatography to give the title compound (745 mg, 1.77 mmol; 87% yield) as a white solid. LCMS, [M+H]+=421; 1H NMR (400M Hz, CDCl3) δ 7.38-7.23 (m, 3H), 7.19-7.08 (m, 3H), 7.04-6.98 (m, 2H), 6.87 (ddd, J=8.0, 2.3, 1.0 Hz, 1H), 3.88 (s, 2H), 3.07 (s, 2H), 2.18-1.95 (m, 4H), 1.87-1.68 (m, 4H).

Provenance & Evidence