N-bromobutanimide → 4-(Bromomethyl)-2-methoxybenzonitrile

HRID 8920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 8920
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OCC)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:11][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([O:2][CH3:1])[CH:10]=1

Komponenten

6

Edukt 2

HCID 67184N-bromobutanimideHCID 124953732-Methoxy-4-methylbenzonitrile

Produkt 1

HCID 219850074-(Bromomethyl)-2-methoxybenzonitrileAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 7187Benzoyl PeroxideKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a solution of 2-methoxy-4-methylbenzonitrile (0.438 g, 2.98 mmol) in CCl4 (6 mL) was added recrystallized N-bromosuccinimide (0.544 g, 3.05 mmol) followed by benzoyl peroxide (47 mg, 0.19 mmol). The resultant mixture was heated to reflux for 45 minutes then cooled to room temperature. The mixture was diluted with diethyl ether (30 mL), filtered through filter paper, and the filtrate was concentrated. Purification of the crude material by column chromatography (6:1 hexanes-EtOAc) provided 0.46 g (68%) of 4-(bromomethyl)-2-methoxybenzonitrile as a white solid. 1H NMR (CDCl3) δ 3.96 (s, 3H), 4.45 (s, 2H), 6.99 (s, 1H), 7.03 (d, 1H, J=9 Hz), 7.53 (d, 1H, J=9 Hz).

Aufarbeitung

  1. temperatureto reflux for 45 minutes
  2. filtrationfiltered
  3. filtrationthrough filter paper
  4. concentrationthe filtrate was concentrated
  5. customPurification of the crude material by column chromatography (6:1 hexanes-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-99fb53d680b64d348c12f770dc6887ea
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091217B2

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