Reaction #2446133

Reaction equation

ether

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

N-bromosuccinimide

water

→

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

Solvents

DMF

DMF

Conditions

Workup

1. 1
   Extractionthe solution was extracted with ethyl acetate (3×150 ml)
2. 2
   WashThe organic phase was washed with water (2×200 ml)
3. 3
   Dryingdried over MgSO4
4. 4
   Otherevaporated
5. 5
   Otheraffording a yellow solid which
6. 6
   Otherwas purified

Procedure

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.

Source