Reacción #509307

Ecuación de reacción

N,N′-dimethyl ethylenediamine

1-bromo-3-methoxy-5-methylbenzene

NaI

→

1-iodo-3-methoxy-5-methylbenzene

Rendimiento 87.0%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrodried
2. 2
   Otrosealed tube
3. 3
   Otrothe tube sealed with a rubber septum
4. 4
   Otroflushed with a stream of nitrogen for 15 min
5. 5
   Otrocap
6. 6
   Temperaturathe sealed tube was heated at 110° C. in an oil bath for 18 h
7. 7
   Temperaturato cool to room temperature
8. 8
   Otroquenched with a saturated aqueous solution of ammonium chloride
9. 9
   ExtracciónThe reaction mixture was extracted with CH2Cl2
10. 10
    LavadoThe organic layer was washed with water
11. 11
    Concentraciónconcentrated to dryness

Procedimiento

Cu(I)I (0.05 g, 0.25 mmol) and NaI (1.49 g, 10 mmol) were added to an oven dried sealed tube and the tube sealed with a rubber septum and flushed with a stream of nitrogen for 15 min. Anhydrous dioxane (5 mL), N,N′-dimethyl ethylenediamine (0.055 mL, 0.50 mmol) and 1-bromo-3-methoxy-5-methylbenzene (1) (1.0 g, 5.0 mmol) were added via a syringe with vigorous stirring under a stream of nitrogen at room temperature. The rubber septum was replaced with the Teflon cap and the sealed tube was heated at 110° C. in an oil bath for 18 h. The reaction was allowed to cool to room temperature and then quenched with a saturated aqueous solution of ammonium chloride. The reaction mixture was extracted with CH2Cl2. The organic layer was washed with water, and then concentrated to dryness to give 1-iodo-3-methoxy-5-methylbenzene (2) (1.05 g, 87% yield) as a pale yellow oil.

Fuente