Reaktion #72450

Reaktionsgleichung

ether

3,4-dihydro-1H-quinolin-2-one

N-bromosuccinimide

water

→

6-Bromo-3,4-dihydro-1H-quinolin-2-one

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe solution was extracted with ethyl acetate (3×150 ml)
2. 2
   WaschenThe organic phase was washed with water (2×200 ml)
3. 3
   Trocknendried over MgSO4
4. 4
   Sonstigeevaporated
5. 5
   Sonstigeaffording a yellow solid which
6. 6
   Sonstigewas purified

Vorschrift

To a solution of 3,4-dihydro-1H-quinolin-2-one (10.0 g, 67.9 mmol) in 100 ml dry DMF was added dropwise a solution of N-bromosuccinimide (12.7 g, 71.3 mmol) in 150 ml dry DMF at 0° C. The mixture was stirred at 0° C. for 2 h, then 400 ml water was added and the solution was extracted with ethyl acetate (3×150 ml). The organic phase was washed with water (2×200 ml), then dried over MgSO4 and evaporated, affording a yellow solid which was purified by washing with cold ether providing pure 6-bromo-3,4-dihydro-1H-quinolin-2-one (13.6 g, 60.3 mmol, 89%) as colorless needles.

Quelle