Phenol → 5-Bromo-2-phenoxypyridine

Temperature

0 °C

To a solution of phenol (1.97 g, 20.9 mmol) in N,N-dimethylformamide (100 mL) was added sodium hydride (1.00 g, 20.9 mmol) at 0° C., which was stirred for 5 minutes at 0° C. 2,5-Dibromopyridine (4.50 g, 19.0 mmol) was then added to this reaction solution at 0° C., and stirred for 40 minutes at room temperature. The reaction solution was then stirred for further 3 hours at 120° C. After allowing to room temperature, the reaction solution was partitioned into water and ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=6:1) to obtain the title compound (3.85 g, 81%).

1. stirringstirred for 40 minutes at room temperature
2. stirringThe reaction solution was then stirred for further 3 hours at 120° C
3. customAfter allowing to room temperature
4. customthe reaction solution was partitioned into water and ethyl acetate
5. customThe organic layer was separated
6. washwashed with water and saturated aqueous sodium chloride
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under a reduced pressure
10. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=6:1)

ORD record

ord-34cc0bef7f0243a9b6605e45d5c1d10b

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507530B2