Iodine → HCID 86749182, compound

Participants

Reaction Steps

Iodine (36 mg, 0.14 mmol) in CH2Cl2 (8 mL) was added over a period of 2 h at 0° C. to 7 (85 mg, 0.114 mmol) in CH2Cl2 (12 mL) under argon. Analysis by TLC (1:6CH2Cl2 :hexanes) indicated the disappearance of 7. The solution was warmed to room temperature, washed with NaHSO3 (2×20 mL) and KF (10 mL) solutions, dried (MgSO4), concentrated in vacuo, and the residue purified by flash column chromatography (1:4 CH2Cl2 :hexanes) to give 8 as a yellow solid (56.4 mg, 95% yield): 1H NMR δ 7.52 (d, J=10.5 Hz, 1 H), 7.2-7.4 (m, 10 H), 6.74 (d, J=10.5 Hz, 1 H), 4.11 (s, 2 H), 3.97 (s, 2 H), 0.27 (s, 9 H); 13C NMR δ 143.93, 136.42, 132.89, 129.20, 128.60, 127.62, 127.34, 120.75, 101.91, 95.48, 43.28, 37.36, -0.08; Anal., Calcd for C23H25IS2Si, C, 53.07; H, 4.84. Found C, 53.27; H, 5.00.

Provenance & Evidence