반응 #487559

반응 방정식

sodium carbonate

2-ethyl-5-bromo nitrobenzene

tin(II) chloride dihydrate

→

5-bromo-2-ethylaniline

수율 17.1%

용매

ethyl acetate

ethanol

반응 조건

후처리

1. 1
   온도After cooling to room temperature the solution
2. 2
   workup.ADDITIONis poured
3. 3
   여과is filtered through diatomaceous earth (
4. 4
   세척further washing with ethyl acetate/aqueous sodium carbonate) and the phases
5. 5
   기타separated
6. 6
   추출After additional extraction of the aqueous phase
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   농축then concentrated in vacuo
9. 9
   기타The crude oil is purified by flash column chromatography on silica gel (hexane/ethyl acetate 8:2 ratio)

실험 절차

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.

출처