Dimethylformamide → 3-Bromo-5-(difluoromethoxy)pyridine

Temperature

100 °C

Potassium carbonate (7.13 g) and chlorodifluoroacetic acid (1.75 ml) were added to a DMF solution (40 ml) of 3-bromo-5-hydroxypyridine (3.0 g). The temperature of the obtained mixture was heated to 100° C., and the mixture was then stirred for 24 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with diethyl ether. The organic layer was successively washed with a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, and was then dried over magnesium sulfate, followed by filtration. The solvent was concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography (n-hexane:diethyl ether), so as to obtain the title compound (670 mg).

1. extractionthe obtained mixture was then extracted with diethyl ether
2. washThe organic layer was successively washed with a saturated sodium bicarbonate aqueous solution
3. dry with materiala saturated sodium chloride aqueous solution, and was then dried over magnesium sulfate
4. filtrationfollowed by filtration
5. concentrationThe solvent was concentrated under reduced pressure
6. customthe residue was then purified by silica gel column chromatography (n-hexane:diethyl ether)

ORD record

ord-5c6522966ac3439c8e65e917cd0ed766

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268848B2