Sodium Iodide → 4-(1-Fluoroethyl)-2-iodopyridine

Temperature

80 °C

2-Chloro-4-(1-fluoroethyl)pyridine (70 g, 439 mmol, 1.00 equiv), NaI (661 g, 4.41 mol, 10.00 equiv), ACN (700 mL) and acetyl chloride (56 g, 713 mmol, 1.60 equiv) were combined in a 2000-mL 4-necked round-bottom flask. The resulting solution was stirred overnight at 80° C. in an oil bath and then cooled to r.t, diluted with ice aqueous saturated sodium carbonate (500 mL) and extracted with dichloromethane (3×500 mL). The combined organic layer was washed with NaS2O3 (10%, 3×300 mL) and the aqueous phase was extracted with dichloromethane (2×200 mL). The combined organic layer was washed with brine (2×500 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography on silica gel column (1:10 ethyl acetate/petroleum ether) to afford 4-(1-fluoroethyl)-2-iodopyridine as yellow oil.

1. temperaturecooled
2. extractionextracted with dichloromethane (3×500 mL)
3. washThe combined organic layer was washed with NaS2O3 (10%, 3×300 mL)
4. extractionthe aqueous phase was extracted with dichloromethane (2×200 mL)
5. washThe combined organic layer was washed with brine (2×500 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under vacuum
8. customThe residue was purified by column chromatography on silica gel column (1:10 ethyl acetate/petroleum ether)

ORD record

ord-53b58e20354b40bc9963f7e0723fc49d

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242984B2