Azobisisobutyronitrile → 3-(Bromomethyl)biphenyl

HRID 1422332

Reaktionsgleichung

Reaktionsgleichung von HRID 1422332
[C:1]1([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 6547Azobisisobutyronitrile2×HCID 125643-MethylbiphenylHCID 67184N-bromobutanimide

Produkt 1

HCID 38644053-(Bromomethyl)biphenyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 3-phenyltoluene (1.80 mL, 10.9 mmol) in carbon tetrachloride (50 mL) was added N-bromosuccinimide (2.124 g, 11.93 mmol) and the mixture heated to 70° C. AIBN (50 mg, 0.30 mmol) was added and the mixture refluxed for 30 mins. Additional AIBN was added (50 mg, 0.30 mmol) and the mixture refluxed for 16 hours. The reaction was cooled, filtered, and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, 5% EtOAc in hexanes) to afford the title compound as a white solid.

Aufarbeitung

  1. temperaturethe mixture refluxed for 30 mins
  2. temperaturethe mixture refluxed for 16 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customThe residue was chromatographed (Silica gel, 5% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0bc455fdad6c4568b19c27e59f766821
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06080870

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