Azobisisobutyronitrile → 2-(Bromomethyl)-6-chlorobenzonitrile

HRID 1752245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1752245
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:11][CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[C:3]=1[C:4]#[N:5]

Komponenten

6

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 230532-Chloro-6-methylbenzonitrileHCID 67184N-bromobutanimide

Produkt 1

HCID 667339472-(Bromomethyl)-6-chlorobenzonitrileAusbeute 46,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5943Carbon TetrachlorideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-6-methylbenzonitrile (2.0 g, 13 mmol) and N-bromosuccinimide (2.6 g, 15 mmol) in carbon tetrachloride (20 mL) was added azobisisobutyronitrile (0.20 g, 1.2 mmol). The mixture was refluxed for 3 h and then cooled, diluted with dichloromethane and washed with water and brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resultant oil was purified via flash column chromatography (ethyl acetate:hexane, 0:100 to 30:70) to yield white solid product (1.4 g, 46%). 1H NMR (400 MHz, CDCl3) δ 7.43-7.59 (m, 3H), 4.64 (s, 2H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 h
  2. temperaturecooled
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant oil was purified via flash column chromatography (ethyl acetate:hexane, 0:100 to 30:70)

Quellen und Nachweise

ORD-Eintrag
ord-15bbc06972cc442d96d857f173004298
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09163003B2

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