Reaction #6687

Reaction equation

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

Solvents

THF

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture was stirred at that temperature for 1 h and at room temperature for 10 h
2. 2
   Otherquenched with water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   Washwashed with brine
5. 5
   Dryingdried over MgSO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherPurification
8. 8
   Otherby recrystallization from hexane

Procedure

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