Azobisisobutyronitrile → 8-bromomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one

HRID 2255195Notes

Reaction equation

HRID 2255195 reaction equation
[CH3:1][C:2]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)=[CH:8][C:7](=[O:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.O>[Br:20][CH2:1][C:2]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)=[CH:8][C:7](=[O:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 197416578-methyl-2-(3-fluorophenyl)-4H-benzopyran-4-one

Product 1

HCID 197416778-bromomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-oneYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 14.3 g of 8-methyl-2-(3-fluorophenyl)-4H-benzopyran-4-one, 17.2 g of N-bromosuccinimide and 3.5 g of azobisisobutyronitrile (AIBN) in 700 ml of carbon tetrachloride was refluxed for 6.5 hours, cooled to room temperature and stirred overnight and then diluted with 100 ml of water. The solvents were removed in vacuo and the residue recrystallized from hot ethyl acetate to give 16.5 g of 8-bromomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one which was used without further purification.

Workup

  1. temperaturewas refluxed for 6.5 hours
  2. customThe solvents were removed in vacuo
  3. customthe residue recrystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-05a2aea173de4e368516c45d1dd41b2e
Source dataset
uspto-grants-1993_08
Patent number
US05238954

Reaction notes

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