Sodium Iodide → HCID 53788388, Verbindung

Temperatur

90 °C

To a mixture of Pd(OAc)2 (0.12 g, 0.53 mmol), NaHCO3 (0.52 g, 6.19 mmol) and NaI (0.28 g, 1.87 mmol) in 5 mL of HMPA is added 5-bromo-2-chloro-thiophene (1.00 g, 5.06 mmol) and allyl alcohol (1.03 mL, 15.2 mmol). The mixture is heated to 90° C. and stirred for 16 hours. The reaction mixture is cooled to room temperature, diluted with Et2O and washed with water. The organic layer is dried over MgSO4, filtered and concentrated in vacuo. The crude residue is purified by flash column chromatography eluting with a gradient of 10% Et2O/hexanes to 20% Et2O/hexanes to provide the product (0.18 g, 1.03 mmol) as an oil. 1H NMR (CDCl3, 300 MHz) δ9.81 (s, 1H), 6.71 (d, 1H), 6.58 (d, 1H), 3.07 (t, 2H), 2.81 (t, 2H).

1. temperatureThe reaction mixture is cooled to room temperature
2. washwashed with water
3. dry with materialThe organic layer is dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe crude residue is purified by flash column chromatography
7. washeluting with a gradient of 10% Et2O/hexanes to 20% Et2O/hexanes

ORD-Eintrag

ord-3a62767deb3a4916a6a8a10d3e00875f

Quelldatensatz

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07612075B2