Reacción #2383773

ord-26ee7c345b06443cb25915c9be1fb57a

Ecuación de reacción

BrCc1ccc2ccccc2c1CBr
1,2-bis(bromomethyl)naphthalene
O=C1CCC(=O)N1Br
N-bromosuccinimide
CC(C)(C#N)N=NC(C)(C)C#N
2,2′-azobis(isobutyronitrile)
BrCc1c(C(Br)Br)ccc2ccccc12
1-(bromomethyl)-2-(dibromomethyl)naphthalene
Rendimiento 64.0%

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtraciónthe reaction mixture was filtered
  2. 2
    Lavadothe residue was washed with 150 ml of dichloromethane
  3. 3
    workup.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. 4
    Otrowas obtained

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06489046B1uspto-grants-2002_12