Reaktion #6912

Reaktionsgleichung

2-Bromo-4-nitrophenol

3-fluorobenzylalcohol

DIAD

triphenylphosphine

→

title compound

Ausbeute 68.0%

2-Bromo-1-(3-fluorobenzyloxy)-4-nitrobenzene

Ausbeute 68.0%

Lösungsmittel

—

Hexanes

THF

water

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm slowly to rt
2. 2
   SonstigeThe layers were separated
3. 3
   Extraktionthe aqueous layer was extracted with EtOAc (200 mL×2)
4. 4
   Waschenwashed with brine
5. 5
   Trocknenby drying over sodium sulfate
6. 6
   SonstigeThe volatiles were removed in vacuo
7. 7
   workup.ADDITIONthe residual semi-solid was treated with diethyl ether
8. 8
   SonstigeThe solids were removed by filtration
9. 9
   SonstigeThe volatiles from the resulting filtrate were removed in vacuo
10. 10
    Sonstigethe material was purified

Vorschrift

2-Bromo-4-nitrophenol (4.86 g, 0.0223 mol), triphenylphosphine (7.6 g, 0.0290 mol), 3-fluorobenzylalcohol (3.65 g, 0.0290 mol) were combined and dissolved in THF (89 mL). The reaction temperature was cooled to 0° C. and DIAD (4.50 g, 0.0290 mol) was added. The reaction was allowed to warm slowly to rt and stirred for 3 h before it was diluted with water (100 mL) and EtOAc (100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (200 mL×2). The organic extracts were combined and washed with brine, followed by drying over sodium sulfate. The volatiles were removed in vacuo and the residual semi-solid was treated with diethyl ether. The solids were removed by filtration. The volatiles from the resulting filtrate were removed in vacuo and the material was purified using EtOAc:Hexanes (90/10) in a biotage LC system to afford the title compound as a yellow solid (3.73 g, 68% yield). 1H NMR (DMSO-d6) □ 8.43 (d, 1H); 8.26 (m, 1H); 7.45 (m, 1H); 7.38 (d, 1H); 7.30 (m, 2H); 7.17 (m, 1H); 5.39 (s, 2H).

Quelle