2-Bromopyridine → 2-(2-Bromophenyl)pyridine

To a 250 mL flask were charged 2-bromopyridine (4.8 mL, 49 mmol), 2-bromophenylboronic acid (9.85 g, 49 mmol), triphenylphosphine (1.09 g, 4.17 mmol), and ethylene glycol dimethyl ether (55 mL). A homogeneous solution was formed. To this solution was added 2 M K2CO3 (60 mL, 120 mmol). The mixture was purged with nitrogen then Pd(OAc)2 (0.24 g, 1 mmol) was added. The mixture was refluxed for 5 h then cooled to room temperature. The reaction mixture was transferred into a separating funnel and the organic layer was separated and retained. The aqueous phase was extracted with ethyl acetate (EtOAc) (4×100 mL). The combined organic layers were washed with water (200 mL) and brine (200 mL) and dried over MgSO4. Filtration and evaporation produced a dark brown oil, which was purified by chromatography on silica gel with CH2Cl2:heptane=2:1 and CH2Cl2 to provide a light yellow oil, 7.57 g, 65%.

1. customA homogeneous solution was formed
2. customThe mixture was purged with nitrogen
3. temperatureThe mixture was refluxed for 5 h
4. customThe reaction mixture was transferred into a separating funnel
5. customthe organic layer was separated
6. extractionThe aqueous phase was extracted with ethyl acetate (EtOAc) (4×100 mL)
7. washThe combined organic layers were washed with water (200 mL) and brine (200 mL)
8. dry with materialdried over MgSO4
9. filtrationFiltration and evaporation
10. customproduced a dark brown oil, which
11. customwas purified by chromatography on silica gel with CH2Cl2
12. customheptane=2:1 and CH2Cl2 to provide a light yellow oil, 7.57 g, 65%

ORD record

ord-1268eab1d52c4cd79dbd7b64b6f4d911

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06835835B1