Azobisisobutyronitrile → 4-bromo-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

HRID 253151Notes

Reaction equation

HRID 253151 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[C:8]([CH3:15])([CH3:14])[CH2:7][CH2:6]2.[Br:16]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:16][CH:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9](=[O:13])[C:8]([CH3:15])([CH3:14])[CH2:7]1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 155786856-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 668447194-bromo-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-oneYield 86%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of 6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one (3.30 g, 16.2 mmol) and 1-bromopyrrolidine-2,5-dione (2.88 g, 16.2 mmol) in 50 mL of CCl4, was added AIBN (0.265 g, 1.62 mmol). The mixture was heated to reflux for three hours. The reaction was cooled to RT and the reaction was quenched with water (25 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and the residue was purified by column chromatography (0-50% EtOAc/Hexane to provide the title compound as a white solid (3.92 g, 86% yield). MS m/z: 284.2 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for three hours
  3. customthe reaction was quenched with water (25 mL)
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was evaporated
  9. customthe residue was purified by column chromatography (0-50% EtOAc/Hexane

Sources & evidence

ORD record
ord-af7250a4943d48519a1db2e08541aed6
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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