Iodine → HCID 67513096, compound

Participants

Reaction Steps

Sodium metaperiodate (0.971 g, 4.54 mmol) was slowly added to a solution of iodine (3.43 g, 13.5 mmol) in sulfuric acid (86 ml). This was stirred at room temperature for 30 minutes. This dark brown iodinating solution was then slowly added to a solution of methyl 3-(4-fluorophenyl)propanoate (5.20 g, 28.5 mmol) in sulfuric acid (28.5 ml) (pre-cooled to 0° C.) taking care not to let the temperature rise above 30° C. This was stirred for 50 min. further, and then the reaction was quenched by pouring onto 100 mL of stirring ice water. This was extracted with ethyl acetate (2×100 mL) and the combined organic layers were washed with water (100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate and purified via column chromatography on a Biotage 40M column eluting with hexanes (1 CV) followed by a gradient of 0-50% ethyl acetate in hexanes to provide the desired product as a clear colorless liquid. 1H NMR (CDCl3, 500 MHz) δ 7.58 (dd, J=5.8 Hz, 1.9 Hz, 1H), 7.13 (m, 1H), 6.96 (t, J=8.2 Hz, 1H), 3.67 (s, 3H), 2.88 (t, J=7.7 Hz, 2H), 2.61 (t, J=7.7 Hz, 2H).

Provenance & Evidence