Azobisisobutyronitrile → 1-(Bromomethyl)-2-(dibromomethyl)naphthalene

HRID 2296591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2296591
[Br:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][Br:14].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH:13]([Br:15])[Br:14]

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 34035511,2-Bis(bromomethyl)naphthalene

Produkt 1

HCID 123671501-(Bromomethyl)-2-(dibromomethyl)naphthaleneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In 150 ml of carbon tetrachloride, 20 g (64 mmole) of 1,2-bis(bromomethyl)naphthalene and 23 g (130 mmole) of N-bromosuccinimide were suspended. To the obtained suspension, 1.1 g (6.7 mmole) of 2,2′-azobis(isobutyronitrile) was added and the mixture was vigorously stirred at 100° C. for 2 hours. After the reaction was completed, the reaction mixture was filtered and the residue was washed with 150 ml of dichloromethane. The filtrate and the washing were combined. The combined solution was treated by the column chromatography (silica gel/dichloromethane) without additional treatments and 16 g (the yield: 64%) of a white solid of 1-(bromomethyl)-2-(dibromomethyl)naphthalene was obtained.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. washthe residue was washed with 150 ml of dichloromethane
  3. additionThe combined solution was treated by the column chromatography (silica gel/dichloromethane) without additional treatments and 16 g (the yield: 64%) of a white solid of 1-(bromomethyl)-2-(dibromomethyl)naphthalene
  4. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-26ee7c345b06443cb25915c9be1fb57a
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489046B1

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