Benzoyl Peroxide → 1-(3-(Bromomethyl)phenyl)propan-1-one

HRID 1356799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356799
[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=[O:11])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:3]=[C:4]([C:8](=[O:11])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1039653'-Methylpropiophenone

Produkt 1

HCID 185094641-(3-(Bromomethyl)phenyl)propan-1-oneAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

3′-Methylpropiophenone (2.38 g; 16.1 mmol), N-bromosuccinimide (2.78 g; 16.1 mmol), and benzoyl peroxide (0.20 g) were added to carbon tetrachloride (60 ml), and the mixture was heated under reflux for 3 hours. The mixture was brought to room temperature, and insoluble matter was filtered off. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1), to thereby yield 3.48 g of the target compound as pale yellow oily, matter (yield: 95.2%). 1H-NMR (CDCl3, ppm); 1.23 (3H, t, J=1.89 Hz), 3.01 (2H, q, J=1.89 Hz), 4.53 (3H, s), 7.42˜7.70 (2H, m), 7.79˜8.13 (2H, m).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customwas brought to room temperature
  4. filtrationinsoluble matter was filtered off
  5. concentrationThe solvent was concentrated 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-19db3edbae5c4d94a6bba5ed771160b3
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586633B1

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