Réaction #77712

Équation de réaction

water

3-hydroxyaniline

4-fluorobenzotrifluoride

potassium tert-butoxide

→

aniline

Rendement 57.2%

3-(4-TRIFLUOROMETHYLPHENOXY)ANILINE

Rendement 57.2%

Solvants

DMSO

Conditions de réaction

Traitement

1. 1
   Températurecooled to room temperature
2. 2
   ExtractionThe mixture was extracted with ether (3×125 mL)
3. 3
   LavageThe organic phase was washed with 2N sodium hydroxide (2×75 mL) and water (100 mL)
4. 4
   Séchagedried (MgSO4)
5. 5
   Autrethe solvent evaporated
6. 6
   Autreto give a dark oil
7. 7
   workup.DISTILLATIONThis oil was distilled

Mode opératoire

To a stirred solution of 3-hydroxyaniline (6.55 g) and 4-fluorobenzotrifluoride (9.85 g) in DMSO (50 mL) was added in one portion potassium tert-butoxide (7.86 g). The resulting dark solution was heated for 4 hours at 95° C., cooled to room temperature, then poured into water (600 mL). The mixture was extracted with ether (3×125 mL). The organic phase was washed with 2N sodium hydroxide (2×75 mL) and water (100 mL), dried (MgSO4) and the solvent evaporated to give a dark oil. This oil was distilled to give the title aniline as a colorless oil (8.7 g), b.p. 110-112° C. at 0.15 mm.

Source