Potassium Carbonate → HCID 68840320, compound

Temperature

140 °C

3-Fluorobenzonitrile (4.4 mL, 40 mmol), 4-bromopyrazole (6 g, 40 mmol) and potassium carbonate (11 g, 80 mmol) were weighed into a flask and flushed with Ar(g). Dry DMF (80 mL) was added and the reaction mixture was stirred at 140° C. for 18 h. The reaction mixture was then cooled to rt and partitioned between EtOAc (200 mL) and brine (100 mL). The organic layer was separated and the aqueous layer was washed with EtOAc (3×150 mL), the combined organic layers were washed with brine (3×50 mL), dried over Na2SO4, filtered and concentrated to afford a solid. This was recrystallized from EtOAc/hexane to give 3-(4-bromo-1H-pyrazol-1-yl)benzonitrile as a beige solid.

1. customflushed with Ar(g)
2. additionDry DMF (80 mL) was added
3. temperatureThe reaction mixture was then cooled to rt
4. custompartitioned between EtOAc (200 mL) and brine (100 mL)
5. customThe organic layer was separated
6. washthe aqueous layer was washed with EtOAc (3×150 mL)
7. washthe combined organic layers were washed with brine (3×50 mL)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto afford a solid
12. customThis was recrystallized from EtOAc/hexane

ORD record

ord-db841c5b98664c5ebba5aeb81baeecef

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569592B2