Reacción #56927

Ecuación de reacción

Sulfuric acid

sodium sulfite

sodium periodate

iodine

acetic anhydride

sodium hydroxide

1-chloro-4-ethyl benzene

sodium chloride

→

4-chloro-1-ethyl-2-iodo-benzene

Rendimiento 76.1%

Disolventes

water

acetic acid

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   SecadoThe organic layer was dried over sodium sulfate
2. 2
   Concentraciónconcentrated under reduced pressure
3. 3
   workup.DISTILLATIONThe residual oil was purified by vacuum distillation (95-100° C., 5-10 mm)

Procedimiento

A mixture of sodium periodate (12 g, 56 mmol), iodine (9.5 g, 37 mmol), acetic acid (80 ml) and acetic anhydride (40 ml) was cooled to 0° C. Sulfuric acid (18 ml) was added dropwise followed by 1-chloro-4-ethyl benzene (15 ml, 110 mmol) dropwise. After stirring for 18 hours, a solution of sodium sulfite (20 g) in water (300 ml) was added. The mixture was adjusted to about pH 7 by addition of 50% aqueous sodium hydroxide solution and treated with ethyl acetate (200 ml) and saturated aqueous sodium chloride solution (200 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residual oil was purified by vacuum distillation (95-100° C., 5-10 mm) followed by flash chromatography on silica gel eluting with hexane to afford 4-chloro-1-ethyl-2-iodo-benzene (7.5 g, 25% yield) as a colorless oil.

Fuente