Dimethylformamide → 5-Bromo-2-(2-fluorophenoxy)pyridine

To a mixture of 2-fluorophenol (2.1 g, 19 mmol), 2,5-dibromopyridine (3.0 g, 13 mmol) and N,N-dimethylformamide (30 mL) was added sodium hydride (730 mg, 15 mmol, 50% in oil) at 0° C., which was stirred for 10 minutes at room temperature. The reaction mixture was then stirred for 5 hours at 110° C. The reaction mixture was cooled to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was washed twice with water and then washed with saturated aqueous sodium chloride, was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=15:1) to obtain the title compound (940 mg, 28%).

1. stirringThe reaction mixture was then stirred for 5 hours at 110° C
2. temperatureThe reaction mixture was cooled to room temperature
3. extractionfollowed by extraction with ethyl acetate
4. washThe organic layer was washed twice with water
5. washwashed with saturated aqueous sodium chloride
6. concentrationwas concentrated under a reduced pressure
7. customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=15:1)

ORD-Eintrag

ord-eb787e56912f454bb24363cbda283138

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08841327B2