Sodium Iodide → HCID 403767, compound

Participants

Reaction Steps

NaI (217 mg, 1.45 mmol) was added to a suspension of bromide 19 (70 mg, 0.15 mmol) in acetone (15 mL). The reaction mixture was heated at reflux for 12 h, after which the resulting orange precipitate was collected by vacuum filtration and purified by flash chromatography (silica gel, CHCl3) to provide 24 (73.0 mg, 95%) as an orange solid: mp 173-174.5° C.; IR (KBr) 2944, 1612, 1522, 1481, 1254, 1033 cm−1; 1H NMR (500 MHz, CDCl3) δ 7.88 (s, 1H), 7.43 (s, 1H), 7.40 (s, 1H), 7.36 (s, 1 H), 6.84 (t, J=7.22 Hz, 1H), 6.05 (s, 2H), 4.08 (s, 3H), 4.04 (s, 3H), 4.00 (s, 3H), 3.35 (t, J=6.69 Hz, 2H), 2.95 (q, J=7.32 Hz, 2H), 2.19 (m, 2H); ESIMS m/z (rel intensity) 532.1 (100, MH+). Anal. Calcd for C24H22INO5: C, 54.25; H, 4.17; N, 2.64. Found: C, 54.64; H, 4.25; N, 2.60.

Provenance & Evidence