Reacción #582200

Ecuación de reacción

n-Butyl lithium

2-Chloro-4,6-difluoroanisole

iodine

NaHSO3

→

1-chloro-3,5-difluoro-4-iodo-2-methoxybenzene

Rendimiento 92.6%

Disolventes

Et2O

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring for 20 minutes
2. 2
   Temperaturato warm to 25° C. over 40 minutes
3. 3
   Otroto destroy excess iodine
4. 4
   ExtracciónThe separated aqueous phase was extracted with 20 mL Et2O
5. 5
   LavadoThe combined ether phases were washed with saturated NaCl
6. 6
   Otrodried
7. 7
   Otroevaporated

Procedimiento

2-Chloro-4,6-difluoroanisole (2.0 g, 11 mmol) was dissolved in 20 mL anhydrous THF and cooled to −70 to −75° C. 2.5M n-Butyl lithium in hexanes (6.7 mL, 17 mmol) was added dropwise. After stirring for 75 minutes at −75° C., the mixture was treated dropwise with a solution of iodine (5.1 g, 20 mmol) in 10 mL THF. After stirring for 20 minutes, the reaction solution was allowed to warm to 25° C. over 40 minutes. The reaction mixture was diluted with Et2O (50 mL) and stirred with dilute NaHSO3 solution to destroy excess iodine. The separated aqueous phase was extracted with 20 mL Et2O. The combined ether phases were washed with saturated NaCl, dried, and evaporated to give 1-chloro-3,5-difluoro-4-iodo-2-methoxybenzene (3.1 g, 91% yield): mp 62-64° C.; GC-MS (m/z=304).

Fuente