N-bromobutanimide → Ethyl 2-(3-(bromomethyl)phenyl)acetate

HRID 1866928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866928
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1)[CH3:2].[Br:14]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:12][C:8]1[CH:7]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])[CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 96574Ethyl m-tolylacetate

Produkt 1

HCID 10563066Ethyl 2-(3-(bromomethyl)phenyl)acetateAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a mixture of m-tolylacetic acid ethyl ester (3.0 g, 16.8 mmol) and N-bromosuccinimide (3.0 g, 16.8 mmol) was added carbon tetrachloride (45 mL), followed by benzoyl peroxide (5 mg), and the reaction mixture was heated at reflux for 16 h. The reaction mixture was cooled to room temperature, filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, eluent 5:95 to 2:3 EtOAc/hexanes) afforded ethyl (3-bromomethylphenyl)acetate as an off-white solid (0.89 g, 21%): 1H NMR (300 MHz, CDCl3) δ 7.32-7.21 (m, 4H), 4.48 (s, 2H), 4.16 (q, J=6 Hz, 2H), 3.63, (s, 2H), 1.27 (t, J=6 Hz, 3H).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, eluent 5:95 to 2:3 EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f423721a9ca5465eb38c5287eab7be58
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629363B2

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