Iodine → HCID 121004314, compound

Participants

Reaction Steps

Silver sulfate (3.47 g, 11.12 mmol) and iodine (0.576 mL, 11.12 mmol) were added successively to a solution of ethyl (1S,2S)-2-(4-methoxyphenyl)cyclopropanecarboxylate (2.45 g, 11.12 mmol) in EtOH (55.6 mL) at 25° C. and the reaction was stirred vigorously for 4 h. After this time the reaction mixture was filtered through a plug of Celite®. The filtrate was diluted with EtOAc (100 mL), washed with water (2×25 mL), aq. NaHSO3 (2×25 mL), and brine (25 mL), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 20% EtOAc in hexanes over 2088 mL) to afford ethyl (1S,2S)-2-(3-iodo-4-methoxyphenyl)cyclopropanecarboxylate, as a colorless oil. Rf=0.61 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3): δ 7.50 (d, J=2.3 Hz, 1H); 7.04 (dd, J=8.5, 2.3 Hz, 1H); 6.71 (d, J=8.5 Hz, 1H); 4.15 (q, J=7.2 Hz, 2H); 3.83 (s, 3H); 2.44-2.39 (m, 1H); 1.82-1.78 (m, 1H); 1.55-1.50 (m, 1H); 1.27 (t, J=7.2 Hz, 3H); 1.25-1.19 (m, 1H).

Provenance & Evidence