Iodine → HCID 178500711, compound

Participants

Reaction Steps

Silver sulfate (0.149 g, 0.478 mmol) and iodine (0.025 mL, 0.478 mmol) were added successively to a solution of methyl [trans-3-(4-methoxyphenyl)cyclobutyl]acetate (0.1119 g, 0.478 mmol) in MeOH (2.4 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 (50 mL), washed with water (2×10 mL), aq. Na2SO3 (2×10 mL), and brine (10 mL), dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Biotage Horizon, 25M, Si, ˜20 mL/min, 100% hexanes for 144 mL, gradient to 20% EtOAc in hexanes over 2394 mL) to afford methyl [trans-3-(3-iodo-4-methoxyphenyl)cyclobutyl]acetate, as a colorless oil. Rf=0.45 (20% EtOAc/hexanes), LCMS calc.=383.01. found=382.92 (M+Na). 1H NMR (500 MHz, CDCl3): δ 7.64 (d, J=2.2 Hz, 1H); 7.16 (dd, J=8.4, 2.2 Hz, 1H); 6.76 (d, J=8.4 Hz, 1H); 3.85 (s, 3H); 3.68 (s, 3H); 3.56-3.46 (m, 1H); 2.74-2.66 (m, 1H); 2.60 (d, J=7.9 Hz, 2H); 2.35-2.27 (m, 2H); 2.17-2.10 (m, 2H).

Provenance & Evidence