Azobisisobutyronitrile → 2-(Bromomethyl)-4-fluorobenzonitrile

HRID 1157524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1157524
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.C1C(=O)N([Br:18])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:10][C:4]1[CH:3]=[C:2]([F:1])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 38260554-Fluoro-2-methylbenzonitrile

Produkt 1

HCID 219849902-(Bromomethyl)-4-fluorobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 4-fluoro-2-methylbenzonitrile (2 g, 14.8 mmol), NBS (2.64 g, 15 mmol) and AIBN (100 mg) in CCl4 was refluxed under nitrogen for 2 hours. The reaction was cooled to room temperature. The solid was removed by filtration. The organic solution was concentrated to give crude product as an oil, which was used in the next step without further purification. 1H-NMR (400 MHz, CDCl3): δ 7.68 (dd, J=5.2, 8.4 Hz, 1H), 7.28 (dd, J=2.4, 8.8 Hz, 1H), 7.12 (m, 1H), 4.6 (s, 2H).

Aufarbeitung

  1. temperaturewas refluxed under nitrogen for 2 hours
  2. customThe solid was removed by filtration
  3. concentrationThe organic solution was concentrated
  4. customto give crude product as an oil, which
  5. customwas used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-8b78b12fad994857bd6a75415869b62e
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807689B2

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