4-Bromo-2-fluoropyridine → 4-Bromo-2-isopropoxypyridine

Temperature

80 °C

To the stirred solution of 4-bromo-2-fluoro-pyridine 17BV (4.12 g, 23.41 mmole) in 50 mL anhydrous IPA in a 150 mL pressure vessel was added 2.627 g (23.41 mmole) of solid potassium tert-butoxide under dry N2 gas. The pressure vessel was tightly sealed and heated at 80° C. for 3 hours. The pressure vessel was cooled to 0° C. in ice-bath before opening. The contents of the pressure vessel were transferred to 250 mL RBF and concentrated to a small volume. The resulting mixture was partitioned between EtOAc and H2O. The organic phase was separated, washed with saturated NaCl solution and dried over MgSO4. The solvent was evaporated and resulting clear oil was purified on RediSep 80 g cartridge eluting with 20:1 Hexanes/EtOAc to give clear oil 18BV (4.2 g, 83%).

1. customThe pressure vessel was tightly sealed
2. temperatureThe pressure vessel was cooled to 0° C. in ice-bath
3. concentrationconcentrated to a small volume
4. customThe resulting mixture was partitioned between EtOAc and H2O
5. customThe organic phase was separated
6. washwashed with saturated NaCl solution
7. dry with materialdried over MgSO4
8. customThe solvent was evaporated
9. customresulting clear oil
10. customwas purified on RediSep 80 g cartridge
11. washeluting with 20:1 Hexanes/EtOAc
12. customto give clear oil 18BV (4.2 g, 83%)

ORD record

ord-ab3888f3405f4912be0d55870412935d

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716483B2