Reacción #74646

Ecuación de reacción

N-iodosuccinamide

4-chloro-3-fluorophenol

sulphuric acid

→

desired product

Rendimiento 54.0%

4-chloro-5-fluoro-2-iodophenol

Rendimiento 54.0%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITthe reaction mixture was left
2. 2
   OtroThe reaction was quenched by addition of water (30 mL)
3. 3
   Extracciónthe compound was extracted into dichloromethane (3×30 mL)
4. 4
   LavadoThe combined organic layers were washed with 10% sodium metabisulphite aqueous solution (2×20 mL)
5. 5
   Secadosaturated aqueous sodium chloride solution, dried over anhydrous magnesium sulphate
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated in vacuo
8. 8
   OtroThe crude material was purified by flash column chromatography (silica, toluene)

Procedimiento

To a suspension of N-iodosuccinamide (6.1 g, 27.3 mmol) in glacial acetic acid (23 mL) was added 4-chloro-3-fluorophenol (4.0 g, 27.3 mmol) and after 5 minutes sulphuric acid was added (0.5 mL, 8.2 mmol) and the reaction mixture was left to stir at room temperature for 16 hours. The reaction was quenched by addition of water (30 mL) and the compound was extracted into dichloromethane (3×30 mL). The combined organic layers were washed with 10% sodium metabisulphite aqueous solution (2×20 mL), then saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo. The crude material was purified by flash column chromatography (silica, toluene) to afford the desired product as an oil (4.0 g, 54%).

Fuente