Bromoacetyl bromide → 6-(Bromoacetyl)-5-fluoro-3,4-dihydro-2(1H)-quinolinone

HRID 50859Notes

Reaction equation

HRID 50859 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][CH2:6][C:7](Br)=[O:8].[F:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH2:13][CH2:14][C:15](=[O:21])[NH:16]2>ClCCCl>[Br:5][CH2:6][C:7]([C:20]1[C:11]([F:10])=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:21])[CH2:14][CH2:13]2)=[O:8]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) ChlorideHCID 227369425-Fluoro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 227369446-(Bromoacetyl)-5-fluoro-3,4-dihydro-2(1H)-quinolinoneYield 29.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

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.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated in vacuo
  3. customthe residue was quenched with ice-water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-b6fd14e045154b0b80bb7c1c5414de80
Source dataset
uspto-grants-2004_03
Patent number
US06713490B2

Reaction notes

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