Reacción #2123925

Ecuación de reacción

5-bromo-2-nitrophenol

benzyl bromide

potassium carbonate

→

2-(benzyloxy)-4-bromo-1-nitrobenzene

Rendimiento 97.0%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato reflux for 5 h
3. 3
   Concentraciónthe reaction mixture was concentrated in vacuo
4. 4
   workup.ADDITIONdiluted with water
5. 5
   Extracciónextracted with ethyl acetate
6. 6
   LavadoThe organic layer was washed with brine
7. 7
   Secadodried over sodium sulfate
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   OtroThe crude material was purified by flash column chromatography (9:1 hexanes/ethyl acetate)

Procedimiento

A mixture of 5-bromo-2-nitrophenol (10.4 g, 47.7 mmol), benzyl bromide (9.8 g, 57.2 mmol) and potassium carbonate (9.9 g, 71.5 mmol) was taken up in acetone (50 mL) and heated to reflux for 5 h. After cooling to ambient temperature, the reaction mixture was concentrated in vacuo, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography (9:1 hexanes/ethyl acetate) to give 2-(benzyloxy)-4-bromo-1-nitrobenzene (14.19 g, 97%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.76 (d, J=8.4 Hz, 1H), 7.32-7.48 (m, 5H), 7.30 (d, J=1.8 Hz, 1H), 7.19 (dd, J=8.7, 1.8 Hz, 1H), 5.23 (s, 2H).

Fuente