Reaction #487559

Reaction equation

sodium carbonate

2-ethyl-5-bromo nitrobenzene

tin(II) chloride dihydrate

→

5-bromo-2-ethylaniline

Yield 17.1%

Solvents

ethyl acetate

ethanol

Conditions

Workup

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

Procedure

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.

Source