Reacción #52908

Ecuación de reacción

Water

n-BuLi

1,3-Dimethoxybenzene

(MeO)3B

→

2,6-dimethoxybenzeneboronic acid

Disolventes

acetic acid

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawarmed to room temperature
2. 2
   workup.STIRRINGstirred for 1 h
3. 3
   TemperaturaThe resulting mixture was cooled again to −78° C.
4. 4
   Temperaturato warm to room temperature
5. 5
   workup.STIRRINGstirred overnight
6. 6
   workup.STIRRINGthe mixture was stirred for 0.5 h
7. 7
   Extracciónextracted with EtOAc
8. 8
   SecadoThe extract was dried (MgSO4)
9. 9
   Otroevaporated

Procedimiento

1,3-Dimethoxybenzene (4 g) was dissolved in freshly distilled THF (10 mL). This solution was cooled to −78° C. and n-BuLi (24 mL, 1.6 M solution in hexanes) was added dropwise to the cold solution. The mixture was stirred at −78° C. for 1 h, then warmed to room temperature and stirred for 1 h. The resulting mixture was cooled again to −78° C. and (MeO)3B (6.7 mL) was added. The mixture was allowed to warm to room temperature and stirred overnight. Water (10 mL) was added, and the mixture was stirred for 0.5 h, acidified to pH 4 with acetic acid and extracted with EtOAc. The extract was dried (MgSO4) and evaporated to give 2,6-dimethoxybenzeneboronic acid, which was used without further purification.

Fuente