Réaction #6687

Équation de réaction

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-Difluoro-4-(4-pentyloxybutoxy)phenylboronic acid

Solvants

THF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe reaction mixture was stirred at that temperature for 1 h and at room temperature for 10 h
2. 2
   Autrequenched with water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   Lavagewashed with brine
5. 5
   Séchagedried over MgSO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   AutrePurification
8. 8
   Autreby recrystallization from hexane

Mode opératoire

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 h,. 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%).

Source