3-Methylacetophenone → 1-(3-(Bromomethyl)phenyl)ethan-1-one

HRID 1356777

Reaktionsgleichung

Reaktionsgleichung von HRID 1356777
[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[Br:11]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 114553-MethylacetophenoneHCID 67184N-bromobutanimide

Produkt 1

HCID 154798071-(3-(Bromomethyl)phenyl)ethan-1-oneAusbeute 38,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

3′-Methylacetophenone (5.00 g; 37.3 mmol), N-bromosuccinimide (6.63 g; 37.3 mmol), and benzoyl peroxide (100 mg) were added to carbon tetrachloride (70 ml), and the mixture was refluxed for 1 hour. The mixture was left to cool to room temperature, and crystals that precipitated were removed by filtration. The filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1), to thereby yield 3.08 g of the target compound (yield: 38.8%).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 hour
  2. waitThe mixture was left
  3. customcrystals that precipitated
  4. customwere removed by filtration
  5. customThe filtrate was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-fabc5a7317ba403681b8e1ab8e4315af
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586633B1

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