Ethyl Acetate → 2-Fluoro-4-vinylpyridine

Temperature

80 °C

A mixture of 2-fluoro-4-iodopyridine (2.23 g, 10.0 mmol), tributyl vinyl tin (3.8 g, 12 mmol), and Pd2Cl2(PPh3)2 (703 mg, 1.0 mmol) in dioxane (20 mL) was heated under nitrogen at 80° C. overnight. After cooled, ethyl acetate (40 ml) and saturated KF aqueous solution were added to the reaction mixture. The mixture was stirred for 30 min. The organic layer was separated and washed with water, dried (MgSO4), and concentrated. The resulting residue was purified by flash column chromatography eluting with hexane/ethyl acetate (20:1) to provide the title compound (463 mg, 38%). 1HNMR (500 MHz, CDCl3) δ ppm 5.55 (d, J=10.92 Hz, 1 H) 5.99 (d, J=17.47 Hz, 1 H) 6.67 (dd, J=17.47, 10.61 Hz, 1 H) 6.88 (m, 1 H) 7.17 (dt, J=5.30, 1.56 Hz, 1 H) 8.16 (d, J=5.30 Hz, 1 H).

1. temperatureAfter cooled
2. customThe organic layer was separated
3. washwashed with water
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customThe resulting residue was purified by flash column chromatography
7. washeluting with hexane/ethyl acetate (20:1)

ORD record

ord-15f83aae19d748729e005e5e64256fa2

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06831175B2