Reacción #487559

Ecuación de reacción

sodium carbonate

2-ethyl-5-bromo nitrobenzene

tin(II) chloride dihydrate

→

5-bromo-2-ethylaniline

Rendimiento 17.1%

Disolventes

ethyl acetate

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature the solution
2. 2
   workup.ADDITIONis poured
3. 3
   Filtraciónis filtered through diatomaceous earth (
4. 4
   Lavadofurther washing with ethyl acetate/aqueous sodium carbonate) and the phases
5. 5
   Otroseparated
6. 6
   ExtracciónAfter additional extraction of the aqueous phase
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Concentraciónthen concentrated in vacuo
9. 9
   OtroThe crude oil is purified by flash column chromatography on silica gel (hexane/ethyl acetate 8:2 ratio)

Procedimiento

To a solution of 2-ethyl-5-bromo nitrobenzene (9.71 g, 230 mmol) in ethanol (125 ml) is added tin(II) chloride dihydrate (35.72 g, 225.71 mmol), followed by heating at 70° C. for 2 hours. After cooling to room temperature the solution is poured into crushed ice (1 liter) then diluted with ethyl acetate (200 ml). Solid sodium carbonate is cautiously added until pH 7 is achieved, at which stage the viscous mixture is filtered through diatomaceous earth (further washing with ethyl acetate/aqueous sodium carbonate) and the phases separated. After additional extraction of the aqueous phase, all organic phases are combined, dried over anhydrous magnesium sulfate then concentrated in vacuo. The crude oil is purified by flash column chromatography on silica gel (hexane/ethyl acetate 8:2 ratio) to afford 5-bromo-2-ethylaniline (7.89 g) as a brown oil.

Fuente