Reaction #62298

Reaction equation

chlorotrimethylsilane

N,N-diisopropylamine

n-butyllithium

1-bromo-3,4-difluorobenzene

→

title compound

(6-Bromo-2,3-difluorophenyl)trimethylsilane

Solvents

tetrahydrofuran

hexane

tetrahydrofuran

water

ethyl acetate

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGstirred at this temperature for 30 minutes
3. 3
   workup.STIRRINGstirred at this temperature for 30 minutes
4. 4
   Temperatureto warm gradually to room temperature
5. 5
   workup.STIRRINGstirred for a day
6. 6
   Washthe organic layer was washed with saturated brine
7. 7
   Dryingdried over anhydrous magnesium sulfate
8. 8
   Otherthe solvent was evaporated
9. 9
   OtherThe crude product was purified
10. 10
    Otherseparated by silica gel column chromatography (n-hexane)-

Procedure

Under nitrogen atmosphere, to a solution of 18.2 mL of N,N-diisopropylamine in 200 mL of tetrahydrofuran was added 66.0 mL of 1.57 M n-butyllithium in hexane at 0° C., and stirred at this temperature for 10 minutes. After cooling to −78° C., a solution containing 20.0 g of 1-bromo-3,4-difluorobenzene in 100 mL of tetrahydrofuran was added dropwise and stirred at this temperature for 30 minutes, stirred at this temperature for 30 minutes, added dropwise with 32.9 mL of chlorotrimethylsilane, and the reaction solution was allowed to warm gradually to room temperature, and stirred for a day. After diluting with water and ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (n-hexane)-, to afford 20.3 g of the title compound as a colorless oil.

Source