反応 #487559

反応方程式

sodium carbonate

2-ethyl-5-bromo nitrobenzene

tin(II) chloride dihydrate

→

5-bromo-2-ethylaniline

収率 17.1%

溶媒

ethyl acetate

ethanol

反応条件

後処理

1. 1
   温度After cooling to room temperature the solution
2. 2
   workup.ADDITIONis poured
3. 3
   ろ過is filtered through diatomaceous earth (
4. 4
   洗浄further washing with ethyl acetate/aqueous sodium carbonate) and the phases
5. 5
   その他separated
6. 6
   抽出After additional extraction of the aqueous phase
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   濃縮then concentrated in vacuo
9. 9
   その他The crude oil is purified by flash column chromatography on silica gel (hexane/ethyl acetate 8:2 ratio)

実験手順

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.

出典