Azobisisobutyronitrile → 7-Bromomethyl-6-chlorochroman-4-one

HRID 747044Notes

Reaction equation

HRID 747044 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[O:8][CH2:7][CH2:6][C:5]2=[O:13].C1C(=O)N([Br:21])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:12][C:11]1[CH:10]=[C:9]2[C:4]([C:5](=[O:13])[CH2:6][CH2:7][O:8]2)=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 50224746-Chloro-7-Methylchromanone

Product 1

HCID 690773757-Bromomethyl-6-chlorochroman-4-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 6-chloro-7-methyl-chroman-4-one (20 g, 101.71 mmol), NBS (19.9 g, 111.88 mmol), and AIBN (4.17 g, 25.43 mmol) in anhydrous CCl4 (300 mL) was heated at reflux in 24 h. The mixture was cooled, filtered the solid. The filtrate was concentrated and used in the next step without purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux in 24 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered the solid
  5. concentrationThe filtrate was concentrated
  6. customused in the next step without purification

Sources & evidence

ORD record
ord-98a6690227fa40ce860c57bb25e4eee3
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

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