Reacción #2194530

Ecuación de reacción

5-amino-2-chloro-4-fluorothiophenol

sodium hydroxide

water

propargyl chloride

→

4-chloro-2-fluoro-5-propargylthioaniline

Rendimiento 31.9%

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas dropwise added at room temperature (ca. 20° to 25° C.)
2. 2
   OtroThe water layer was separated
3. 3
   Extracciónextracted with ether
4. 4
   ExtracciónThe ether extract
5. 5
   Lavadowashed with water
6. 6
   Otrodried
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe residue was crystallized from methanol

Procedimiento

To a mixture of 5-amino-2-chloro-4-fluorothiophenol (8.4 g), sodium hydroxide (3 g), water (80 ml), diethyl ether (40 ml) and tributylbenzylammonium chloride (0.1 g), propargyl chloride (5.2 g) was dropwise added at room temperature (ca. 20° to 25° C.), and the resultant mixture was stirred at the same temperature for 3 hours. The water layer was separated and extracted with ether. The ether extract was combined with the ether layer, washed with water, dried and concentrated under reduced pressure. The residue was crystallized from methanol to give 3.25 g of 4-chloro-2-fluoro-5-propargylthioaniline. M.P., 58°-59.5° C.

Fuente