Réaction #52227

Équation de réaction

bicarbonate

N-(2,2-dimethoxyethyl)-N-methanesulphonyl-4-fluoro-3-methoxyaniline

→

5-fluoro-1-methanesulphonyl-6-methoxyindole

Solvants

toluene

toluene

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   workup.ADDITIONpoured onto ice/
3. 3
   AutreThe organic layer was separated
4. 4
   Lavagewashed with sat. sod
5. 5
   SéchageThe solution was dried (MgSO4)
6. 6
   Autreevaporated in vacuo

Mode opératoire

To a solution of N-(2,2-dimethoxyethyl)-N-methanesulphonyl-4-fluoro-3-methoxyaniline (1.91 g, 0.65 mmol) in dry toluene at 0° C. under argon, was added slowly a solution of TiCl4 (0.173 g, 0.911 mmol) in dry toluene (10 ml). The solution was then heated to 70° C. for 1 h. cooled and poured onto ice/sat. sod. bicarbonate solution (20 ml). The organic layer was separated, washed with sat. sod. bicarbonate solution, 0.5% hydrochloric acid (2×20 ml) and water (2×20 ml). The solution was dried (MgSO4) and evaporated in vacuo to give 5-fluoro-1-methanesulphonyl-6-methoxyindole ((0.102 g)

Source