4-Chlorobenzonitrile → (1,1'-Biphenyl)-4-carbonitrile

An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol %), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-chlorobenzonitrile (136 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 159 mg (89%) of the title compound.

1. customAn oven dried resealable Schlenk tube
2. customwas evacuated
3. customThe tube was evacuated
4. additionwas added through a rubber septum
5. customThe tube was sealed with a teflon screwcap
6. customhad been completely consumed
7. additionThe reaction mixture was then diluted with ether (30 mL)
8. additionpoured into a separatory funnel
9. washThe mixture was washed with water (20 mL)
10. extractionthe aqueous layer was extracted with ether (20 mL)
11. washThe combined organic layers were washed with brine (20 mL)
12. dry with materialdried over anhydrous magnesium sulfate
13. filtrationfiltered
14. concentrationconcentrated
15. customThe crude material was purified by flash chromatography on silica gel

ORD record

ord-4d95a958ba3c4e9c8aac31fca48d792d

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07223879B2