Benzoyl Peroxide → 3-(Bromomethyl)-4-fluorobenzonitrile

HRID 1360678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360678
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[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][CH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[F:1])[C:6]#[N:7]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27791804-Fluoro-3-methylbenzonitrile

Produkt 1

HCID 162272363-(Bromomethyl)-4-fluorobenzonitrileAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a solution of 4-fluoro-3-methylbenzonitrile (15.0 g, 111 mmol), in CCl4 (600 mL) was added N-bromosuccinimide (23.7 g, 133 mmol), and benzoyl peroxide (5.38 g, 22.2 mol). The mixture was irradiated with a sunlamp (250 W) to create a gentle reflux. After 0.5 hours of exposure the reaction was complete by TLC. The reaction mixture was cooled and filtered through celite. The filtrate was condensed in vacou to yield brown oil. The crude residue was purified via silica gel column chromatography (hexanes/ethyl acetate) to yield 17.7 g of the desired product.

Aufarbeitung

  1. customThe mixture was irradiated with a sunlamp (250 W)
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through celite
  4. customcondensed in vacou
  5. customto yield brown oil
  6. customThe crude residue was purified via silica gel column chromatography (hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e08561509d4340ada56c3f86cd87b461
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879875B2

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