Iodine → HCID 57779776, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried round-bottom flask containing the product of Step 4 (1.92 g, 8.68 mmol) was fitted with a stirbar and septa and flushed with nitrogen. Dichloromethane (50 mL) and N,N′,N′-tetramethylethylenediamine (5.80 mL, 38.4 mmol) were added, giving a solution that was cooled to −10° C. Iodotrimethylsilane (4.80 mL, 35.3 mmol) was added, and stirring was continued at −10° C. for 30 minutes. Iodine (4.71 g, 18.6 mmol) was then added, and the reaction was warmed to 0° C. After stirring 2 hours at 0° C., the reaction was diluted with dichloromethane (100 mL) and washed with 10% aqueous sodium sulfite solution (2×50 mL). The organic layer was then dried over MgSO4, filtered and concentrated in vacuo to give an oil that was purified via flash chromatography on silica gel (0% to 30% ethyl acetate/hexanes linear gradient) to give the desired product.

Provenance & Evidence