Iodine → 2-Fluoro-3-iodo-5-methylpyridine

A solution of 2-fluoro-5-methyl-pyridine (1.0 g, 9.000 mmol) in dry THF (10 mL) was added dropwise and the solution was stirred at this temp for 2 hours. A solution of iodine (2.284 g, 463.3 μL, 9.000 mmol) in THF (10 mL) was then added and the resultant mixture stirred for a further 1 hour at this temp before being quenched with water. The resulting mixture was partitioned between sodium thiosulfate solution and Et2O, organics separated and washed further with saturated NaCl. The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give a colourless oil. The resulting mixture was purified by column chromatography (30% EtOAc in hexanes, ˜200 mL silica) to give a colourless foam (1.409 g, 66% Yield).

1. custombefore being quenched with water
2. customThe resulting mixture was partitioned between sodium thiosulfate solution and Et2O
3. customorganics separated
4. washwashed further with saturated NaCl
5. dry with materialThe combined organics were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto give a colourless oil
9. customThe resulting mixture was purified by column chromatography (30% EtOAc in hexanes, ˜200 mL silica)

ORD record

ord-ce69ffb2ea8b4b17856de9c0bef3dbaa

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367697B2