Réaction #1960509

Équation de réaction

4-Fluorophenylhydrazine hydrochloride

3-methyl-2-butanone

indole

→

indole

Rendement 99.9%

5-fluoro Indole

Rendement 99.9%

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   Autreto obtain the clear solution
2. 2
   AutreAt the end of 40 min.
3. 3
   workup.ADDITIONthe mixture was poured
4. 4
   ExtractionThe residue was extracted into ethyl acetate (100 ml×2)
5. 5
   Lavagewashed with water (100 ml×2) and ethyl acetate layer
6. 6
   Séchagewas dried over anhydrous sodium sulfate
7. 7
   FiltrationAfter filtration, ethyl acetate
8. 8
   Autrewas removed
9. 9
   Autrethe residue was dried

Mode opératoire

A mixture containing 4-Fluorophenylhydrazine hydrochloride (5.0 g; 30.75 mmol; ALDRICH), 3-methyl-2-butanone (3.7 g; 43 mmol; ALDRICH) and acetic acid (30 ml) was stirred for 30 min. under nitrogen to obtain the clear solution. The mixture was then refluxed at 130° C. The appearance of UV-Vis Abs. Max at 255 nm and the disappearance of the peak at 282 nm confirmed the formation of the indole. At the end of 40 min. the reaction was stopped and the mixture was poured into crushed ice (100 g). The residue was extracted into ethyl acetate (100 ml×2), washed with water (100 ml×2) and ethyl acetate layer was dried over anhydrous sodium sulfate. After filtration, ethyl acetate was removed, and the residue was dried to give 4.15 g of the indole (Yield 76%).

Source