Reaktion #6687

Reaktionsgleichung

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred at that temperature for 1 h and at room temperature for 10 h
2. 2
   Sonstigequenched with water
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried over MgSO4
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigePurification
8. 8
   Sonstigeby recrystallization from hexane

Vorschrift

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%).

Quelle