Benzene, 1-bromo-3-nitro- → 1-(3-Nitrophenyl)pyrrolidine

Temperatur

100 °C

To a solution of 3-bromonitrobenzene (2.02 g, 10 mmol) in toluene (33 mL) and pyrrolidine (1.0 mL, 12 mmol) was added sodium t-butoxide (1.92 g, 20 mmol) and the solution was deoxygenated by passing a nitrogen through the solution at room temperature for 15 minutes. BINAP and tris(dibenzylideneacetone)dipalladium(0) complex were subsequently added as a solid and the nitrogen bubbling was continued for an additional 5 minutes. The mixture was heated at 100° C. overnight. The reaction mixture was then cooled and partitioned between water and ethyl acetate. The organic layer was washed once with brine solution and dried over anhydrous sodium sulfate. The ethyl acetate was decanted and evaporated under reduced pressure to give the desired 1-(3-nitrophenyl)pyrrolidine as a red oil (1.5 g, 79%).

1. customthe solution was deoxygenated
2. customat room temperature
3. customfor 15 minutes
4. additionBINAP and tris(dibenzylideneacetone)dipalladium(0) complex were subsequently added as a solid
5. temperatureThe reaction mixture was then cooled
6. custompartitioned between water and ethyl acetate
7. washThe organic layer was washed once with brine solution
8. dry with materialdried over anhydrous sodium sulfate
9. customThe ethyl acetate was decanted
10. customevaporated under reduced pressure

ORD-Eintrag

ord-c1ffa83b8832409caced2f3bcece3ed8

Quelldatensatz

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07288538B2