Bromobenzene → 2-Phenylfuran

Temperature

50 °C

To a 0° C. solution of furan (10.2 g, 0.15 mol) in 100 mL of THF was added 2.5 M n-butyllithium (60 mL, 0.15 mol). The solution was stirred 3 h and the suspension was then added to a solution of zinc chloride (20 g, 0.15 mol) in 100 mL of THF at room temperature and stirred 1 h. In another flask bromobenzene (10.5 mL, 0.10 mol) was added to a solution of tetrakis(triphenylphosphine)palladium(0) (0.57 g, catalytic) in 300 ml THF and to this mixture was added the furyl zinc solution via cannula. The mixture was heated at 50° C. and stirred for 24 h. The reaction was cooled and quenched with 10% aqueous HCl solution (100 mL). The aqueous layer was washed with ether (2×100 mL) and the combined organic extract was washed with saturated sodium bicarbonate solution (100 mL), brine (100 mL), dried over MgSO4, filtered and concentrated. Distillation at 10 torr (b.p. 94° C.) yielded 12.1 g (81%) of 2-phenylfuran.

1. stirringstirred 1 h
2. stirringstirred for 24 h
3. temperatureThe reaction was cooled
4. customquenched with 10% aqueous HCl solution (100 mL)
5. washThe aqueous layer was washed with ether (2×100 mL)
6. extractionthe combined organic extract
7. washwas washed with saturated sodium bicarbonate solution (100 mL), brine (100 mL)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. distillationDistillation at 10 torr (b.p. 94° C.)

ORD record

ord-c7e73d69e94248f0a46ecd8c6bd0ff45

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05112848