Reacción #6693

Ecuación de reacción

triisopropylborate

1,2-difluoro-3-(4-pentyloxybutoxy)-benzene

1,2-Difluoro-3-(4-pentyloxybutoxy)benzene

butyllithium

→

2,3-difluoro-4-(4-pentyloxybutoxy)phenylboronic acid

2,3-Difluoro4-(4-pentyloxybutoxy)phenylboronic acid

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction mixture was stirred at that temperature for 1 h and at room temperature for 10 h
2. 2
   Otroquenched with water
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   Lavadowashed with brine
5. 5
   Secadodried over MgSO4
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroPurification
8. 8
   Otroby recrystallization from hexane

Procedimiento

To a solution of 1,2-difluoro-3-(4-pentyloxybutoxy)-benzene (24), (1 equi.) in THF (5 mL/mmole), butyllithium (1.3 equi.) was added at −78° C. The reaction mixture was stirred at that temperature for 2 hr,. Then triisopropylborate (1 equi.) was added at that temperature. The reaction mixture was stirred at that temperature for 1 h and at room temperature for 10 h, quenched with water, extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by recrystallization from hexane gave 2,3-difluoro-4-(4-pentyloxybutoxy)phenylboronic acid (25), as a white solid (75%).

Fuente