Reacción #60560

Ecuación de reacción

4-bromoaniline

iodobenzene

potassium hydroxide

phenanthroline

→

diphenylamino 4-bromobenzene

Rendimiento 161.9%

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to room temperature
2. 2
   Filtraciónthe insoluble solid salt was filtered off
3. 3
   ExtracciónThe filtrate was extracted with toluene
4. 4
   workup.DISTILLATIONdistilled water two times
5. 5
   Otrothe organic layer was collected
6. 6
   OtroToluene was removed from the organic layer under reduced pressure
7. 7
   Otroto provide an organic compound
8. 8
   OtroThe organic compound was purified by column chromatography
9. 9
   OtroThen, the product was precipitated with a small amount of ethanol

Procedimiento

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+).

Fuente