Reaktion #71034

Reaktionsgleichung

n-BuLi

N2

1,3-dibromobenzene

THF

NH4Cl

→

title compound

1-(3-Bromo-phenyl)-ethanone

Lösungsmittel

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Extraktionthe aq. layer was extracted with Et2O (3×50 mL)
3. 3
   Trocknenextracts were dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigethe solvents were removed under reduced pressure
6. 6
   SonstigePurification of the residue by FC (20:1 hept-EA)

Vorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 1,3-dibromobenzene (2.45 g, 10.07 mmol) in THF (25.0 mL) was treated at −78° C. with n-BuLi (4.0 mL of a 2.5M solution in hexane, 10.00 mmol). The reaction mixture was stirred for 30 min before N,N-dimethylacetaminde (1.50 mL, 16.13 mmol) was added and the solution was then allowed to warm to rt over 1 h. Sat. aq. NH4Cl was then added and the aq. layer was extracted with Et2O (3×50 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (20:1 hept-EA) gave the title compound as a white solid: TLC:rf (10:1 hept-EA)=0.28. LC-MS-conditions 02: tR=0.95 min.

Quelle