Reaction #79137

Reaction equation

aluminum chloride

bromoacetyl bromide

5-Fluoro-3,4-dihydroquinolin-2(1H)-one

→

6-(Bromoacetyl)-5-fluoro-3,4-dihydroquinolin-2(1H)-one

Yield 29.1%

Solvents

1,2-dichloroethane

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Otherthe solvent was evaporated in vacuo
3. 3
   Otherthe residue was quenched with ice-water
4. 4
   Extractionextracted with ethyl acetate
5. 5
   DryingThe extract was dried over sodium sulfate
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherThe residue was purified by column chromatography (hexane/ethyl acetate=1/1)

Procedure

To a stirring suspension of aluminum chloride (8.0 g, 60 mmol) in 1,2-dichloroethane (16 ml) was added bromoacetyl bromide (4.2 ml, 48 mmol) at 0° C. After 30 min, to a suspension was added 5-Fluoro-3,4-dihydroquinolin-2(1H)-one (4.0 g, 24 mmol) portionwise, then the mixture was allowed to warm to 50° C. and stirred for 4 h. After cooling, the solvent was evaporated in vacuo and the residue was quenched with ice-water and extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (hexane/ethyl acetate=1/1) to afford 6-(Bromoacetyl)-5-fluoro-3,4-dihydroquinolin-2(1H)-one (2.0 g) as a yellow solid.

Source