Reaktion #487559

Reaktionsgleichung

sodium carbonate

2-ethyl-5-bromo nitrobenzene

tin(II) chloride dihydrate

→

5-bromo-2-ethylaniline

Ausbeute 17.1%

Lösungsmittel

ethyl acetate

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature the solution
2. 2
   workup.ADDITIONis poured
3. 3
   Filtrationis filtered through diatomaceous earth (
4. 4
   Waschenfurther washing with ethyl acetate/aqueous sodium carbonate) and the phases
5. 5
   Sonstigeseparated
6. 6
   ExtraktionAfter additional extraction of the aqueous phase
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Einengenthen concentrated in vacuo
9. 9
   SonstigeThe crude oil is purified by flash column chromatography on silica gel (hexane/ethyl acetate 8:2 ratio)

Vorschrift

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.

Quelle