Hydrochloric Acid → HCID 58535078, compound

Temperature

115 °C

To a 2-L Chem-Glass reactor was added 2,3-dichloropyridinol (90 g, 0.55 mol), 3,4-difluoronitrobenzene (100 g, 0.63 mol), lithium carbonate (59.4 g, 0.80 mol) and dimethyl sulfoxide (360 mL). The mixture was heated to 115° C. for 21 hrs, until the reaction was deemed complete by HPLC analysis. The mixture was cooled to 25° C. and methanol (180 mL) was added, followed by water (960 mL). The mixture was neutralized by addition of conc. HCl (60 g) and the resulting slurry was stirred at 35° C. for 1 h. After cooling to 28° C., the slurry was filtered on a Buechner funnel and the filter cake was washed with water (four times 250 mL). The crude cake was then suspended in methanol (20 mL) and water (250 mL), and the resulting mixture was stirred for 20 min at 45° C. After cooling to 25° C., the slurry was filtered. The resulting cake washed with heptane (two times 75 mL) and dried under vacuum to yield 164.68 g (99%) of 2,3-dichloro-4-(2-fluoro-4-nitrophenoxy)pyridine as yellow solid.

1. temperatureThe mixture was cooled to 25° C.
2. temperatureAfter cooling to 28° C.
3. filtrationthe slurry was filtered on a Buechner funnel
4. washthe filter cake was washed with water (four times 250 mL)
5. stirringwater (250 mL), and the resulting mixture was stirred for 20 min at 45° C
6. temperatureAfter cooling to 25° C.
7. filtrationthe slurry was filtered
8. washThe resulting cake washed with heptane (two times 75 mL)
9. customdried under vacuum

ORD record

ord-159965c4212d49bb92e074032bd2f96b

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08558000B2