Iodine → HCID 10923457, compound

Temperature

-78 °C

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.

1. customTo a 250 mL round-bottomed flask equipped with a magnetic stir-bar
2. dissolutiondissolved
3. temperaturewas warmed to room temperature
4. filtrationfiltered through a cake of celite
5. washThe resulting brown solution was then washed with 50% aqueous Na2S2O3 (2×80 mL)
6. dry with materialThe organic layer was then dried over Na2SO4
7. customEvaporation of the solvent in vacuo
8. customgave a yellow oil that
9. washwas eluted through a plug of silica gel (hexanes, ca. 400 mL eluent)
10. customto give a colorless solution
11. customEvaporation of the solvent

ORD record

ord-cb70233b1c444fd888bd62623c3e6ca9

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09284270B2