Reacción #52976

Ecuación de reacción

(MeO)3B

n-BuLi

1-Bromo-2,6-dichlorobenzene

Water

→

2,6-dichlorobenzeneboronic acid

Disolventes

HOAc

hexane

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to room temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   workup.STIRRINGthe resulting mixture was stirred for 0.5 h
4. 4
   Extracciónextracted with EtOAc
5. 5
   LavadoThe organic layer was further washed with water and brine
6. 6
   Secadodried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated

Procedimiento

1-Bromo-2,6-dichlorobenzene (2.00 g) was dissolved in freshly distilled THF (7 mL). This solution was cooled to −78° C. and n-BuLi (8.3 mL of a 1.6M solution in hexane) was added dropwise to the cold solution under N2. The mixture was stirred for 5 min at −78° C. and (MeO)3B (2.2 mL) was added. The resulting mixture was allowed to warm to room temperature and stirred overnight. Water was added and the resulting mixture was stirred for 0.5 h, then acidified with HOAc and extracted with EtOAc. The organic layer was further washed with water and brine, dried (MgSO4) filtered and evaporated to yield 2,6-dichlorobenzeneboronic acid (1.6 g).

Fuente