تفاعل #487559

معادلة التفاعل

sodium carbonate

2-ethyl-5-bromo nitrobenzene

tin(II) chloride dihydrate

→

5-bromo-2-ethylaniline

المردود 17.1%

المذيبات

ethyl acetate

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling to room temperature the solution
2. 2
   workup.ADDITIONis poured
3. 3
   ترشيحis filtered through diatomaceous earth (
4. 4
   غسيلfurther washing with ethyl acetate/aqueous sodium carbonate) and the phases
5. 5
   أخرىseparated
6. 6
   استخلاصAfter additional extraction of the aqueous phase
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   تركيزthen concentrated in vacuo
9. 9
   أخرىThe crude oil is purified by flash column chromatography on silica gel (hexane/ethyl acetate 8:2 ratio)

الإجراء التجريبي

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.

المصدر