Azobisisobutyronitrile → 1-Naphthalenecarboxylic acid, 4-(bromomethyl)-, methyl ester

HRID 11858Notes

Reaction equation

[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

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.

Workup

customAfter the completion of the reaction
customthe solid was removed
filtrationfilter
concentrationthe filtrate was concentrated
dissolutionThe residue was dissolved in chloroform
washwashed with 1 mol/l aqueous solution of sodium hydroxide and saturated brine
dry with materialThe solution was dried over anhydrous sodium sulfate
customThe solvent was removed by distillation
customthe residue was dried under reduced pressure

Sources & evidence

ORD record: ord-556b3489715040888ff745b81e37a366
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098215B2

Reaction notes

Loading…