Reaktion #60560

Reaktionsgleichung

4-bromoaniline

iodobenzene

potassium hydroxide

phenanthroline

→

diphenylamino 4-bromobenzene

Ausbeute 161.9%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Filtrationthe insoluble solid salt was filtered off
3. 3
   ExtraktionThe filtrate was extracted with toluene
4. 4
   workup.DISTILLATIONdistilled water two times
5. 5
   Sonstigethe organic layer was collected
6. 6
   SonstigeToluene was removed from the organic layer under reduced pressure
7. 7
   Sonstigeto provide an organic compound
8. 8
   SonstigeThe organic compound was purified by column chromatography
9. 9
   SonstigeThen, the product was precipitated with a small amount of ethanol

Vorschrift

To a 500 ml flask, 17.2 g (0.1 mol) of 4-bromoaniline, 50 g (0.24 mol) of iodobenzene, 32 g (0.8 mol) of potassium hydroxide, 0.04 g (0.04 mol, 0.4 eq.) of cuprous chloride and 0.08 g (0.04 mol, 0.4 eq.) of phenanthroline were introduced and stirred for 12 hours at 180° C. under nitrogen atmosphere. The reaction mixture was cooled to room temperature and the insoluble solid salt was filtered off. The filtrate was extracted with toluene and distilled water two times and then the organic layer was collected. Toluene was removed from the organic layer under reduced pressure to provide an organic compound. The organic compound was purified by column chromatography using n-hexane as an eluent. Then, the product was precipitated with a small amount of ethanol to provide 21 g of diphenylamino 4-bromobenzene (yield 65%). m/z 324 (M+).

Quelle