Reaction #6692

Reaction equation

Sodium hydride

4-(2,3-difluorophenoxy)-butan-1-ol

4-(2,3-Difluorophenoxy)-butan-1-ol

1-bromopentane

→

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

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

Solvents

DMF

Conditions

Workup

1. 1
   Otherquenched with water
2. 2
   Extractionextracted with ethyl acetate:hexane (1:1)
3. 3
   Washwashed with brine
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherPurification by chromatography
7. 7
   Otheron silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile

Procedure

Sodium hydride (1 equi.) was added to the solution of 4-(2,3-difluorophenoxy)-butan-1-ol (22), (1 equi.) and 1-bromopentane (1 equi.) in DMF (1 mL/mmole) and the reaction mixture was stirred at room temperature for 12 h,. quenched with water, extracted with ethyl acetate:hexane (1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile gave 1,2-difluoro-3-(4-pentyloxybutoxy)-benzene (24), as a white solid (84%).

Source