Reaction #2383773

Reaction equation

1,2-bis(bromomethyl)naphthalene

N-bromosuccinimide

2,2′-azobis(isobutyronitrile)

→

1-(bromomethyl)-2-(dibromomethyl)naphthalene

Yield 64.0%

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Filtrationthe reaction mixture was filtered
2. 2
   Washthe 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
   Otherwas obtained

Procedure

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.

Source