Reaction #11954

Reaction equation

compound

Methyl 4-methyl-1-naphthalene Carboxylate

N-bromosuccinimide

azobisisobutylonitrile

→

title compound

Yield 96.6%

Methyl 4-bromomethyl-1-naphthalene Carboxylate

Yield 96.6%

Solvents

carbontetrachloride

Conditions

Workup

1. 1
   OtherAfter the completion of the reaction
2. 2
   Otherthe solid was removed
3. 3
   Filtrationfilter
4. 4
   Concentrationthe filtrate was concentrated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in chloroform
6. 6
   Washwashed with 1 mol/l aqueous solution of sodium hydroxide and saturated brine
7. 7
   DryingThe solution was dried over anhydrous sodium sulfate
8. 8
   OtherThe solvent was removed by distillation
9. 9
   Otherthe residue was dried under reduced pressure

Procedure

The compound obtained in Example 17-1 (269.9 mg) was dissolved in carbontetrachloride (8 ml), and N-bromosuccinimide (252.6 mg) and azobisisobutylonitrile (22.1 mg) were added to the solution. The mixture was stirred for 6 hours at 70° C. After the completion of the reaction, the solid was removed using a glass filter and the filtrate was concentrated. The residue was dissolved in chloroform and washed with 1 mol/l aqueous solution of sodium hydroxide and saturated brine. The solution was dried over anhydrous sodium sulfate. The solvent was removed by distillation and the residue was dried under reduced pressure to obtain the title compound (363.3 mg) as pale yellow oil.

Source