Iodine → HCID 10923457, compound

Participants

Reaction Conditions

Reaction Steps

To a 250 mL round-bottomed flask equipped with a magnetic stir-bar was placed the 3,4-bis(trimethylsilyl)furan (2.00 g, 9.41 mmol) as a solution in THF (138 mL). Silver trifluoroacetate (4.16 g, 18.8 mmol) was added and the mixture was stirred for 5 min at room temperature until the silver salt dissolved. The resulting colorless solution was cooled to −78° C. and I2 was then added as a solution in THF (50 mL) over 10 min. The mixture was stirred at −78° C. for 3 h after which time it was warmed to room temperature diluted with Et2O (200 mL) and then filtered through a cake of celite. The resulting brown solution was then washed with 50% aqueous Na2S2O3 (2×80 mL) followed by saturated aqueous NaHCO3 (50 mL), and then brine (50 mL). The organic layer was then dried over Na2SO4. Evaporation of the solvent in vacuo gave a yellow oil that was eluted through a plug of silica gel (hexanes, ca. 400 mL eluent) to give a colorless solution. Evaporation of the solvent gave (4-iodofuran-3-yl)trimethylsilane as a pale pink oil (2.20 g, 87%). 1H NMR: δ 7.49 (d, 1H, J=1.5 Hz), 7.22 (d, 1H, J=1.5 Hz), 0.30 (s, 9H). Ref.: Song, Z. Z., Wong, H. N. C. Liebigs Ann. Chem. 1994, 29-34.

Provenance & Evidence