Toluene → 4-Fluoro-3'-methoxy-3-nitrobiphenyl

4-Bromo-1-fluoro-2-nitro-benzene (5 gms.), 3.85 gms. 3-methoxyphenylboronic acid and 22 mL of a 2M aqueous solution of sodium carbonate are suspended in 100 mL of a 1:1 (v:v) mix of toluene and ethanol. The resulting suspension is then treated with 0.8 gms. tetrakis(triphenylphosphine)palladium(0) at room temperature. The reaction mixture is then heated at reflux for 12 h. The reaction mixture is subsequently concentrated in vacuo, and the resulting residue is taken up in ethyl acetate (200 mL). The ethyl acetate solution is then washed successively with water (2×200 mL), and brine (2×200mL). The organic layer is then dried by filtering through phase separator paper and concentrated in vacuo to yield 7.19 gms. of crude product. The crude product is then recrystallized from hot ethanol yielding 4-fluoro-3′-methoxy-3-nitro-biphenyl as a yellow-white solid in the amount of 4.767 gms.

1. additionThe resulting suspension is then treated with 0.8 gms
2. customat room temperature
3. temperatureThe reaction mixture is then heated
4. temperatureat reflux for 12 h
5. concentrationThe reaction mixture is subsequently concentrated in vacuo
6. washThe ethyl acetate solution is then washed successively with water (2×200 mL), and brine (2×200mL)
7. customThe organic layer is then dried
8. filtrationby filtering through phase
9. concentrationconcentrated in vacuo
10. customto yield 7.19 gms
11. customThe crude product is then recrystallized from hot ethanol

ORD-Eintrag

ord-842c8a1fc9d040ed9e1571297c6d1a76

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07098236B2