Reacción #74644

Ecuación de reacción

N-iodosuccinimide

3-chloro-4-fluorophenol

heptane

sulphuric acid

→

title compound

Rendimiento 64.2%

5-chloro-4-fluoro-2-iodophenol

Rendimiento 64.2%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe mixture was concentrated in vacuo
2. 2
   Otrothe residue was partitioned between water and dichloromethane
3. 3
   Secadothe dichloromethane was dried over anhydrous magnesium sulphate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   Otroto give an orange/red oil
7. 7
   OtroThe crude product was purified by column chromatography on silica gel using 1:1 ethyl acetate

Procedimiento

N-iodosuccinimide (4.61 g, 20.5 mmol), was suspended in glacial acetic acid (20 ml). To this suspension was added 3-chloro-4-fluorophenol (3.0 g, 20.0 mmol) and then concentrated sulphuric acid (0.36 ml, 6.14 mmol) was added dropwise over 5 minutes. The resulting brown/orange suspension was stirred at room temperature for 18 hours. The mixture was concentrated in vacuo and the residue was partitioned between water and dichloromethane, the dichloromethane was dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give an orange/red oil. The crude product was purified by column chromatography on silica gel using 1:1 ethyl acetate:heptane to give the title compound as a pale orange/brown solid (3.50 g, 60% yield)

Fuente