N-bromobutanimide → 1-Bromo-2-(4-methylsulfonylphenyl)-3-phenylazulene

HRID 1456827Notes

Reaction equation

HRID 1456827 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:20]=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Br:27]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:27][C:20]1[C:19]2[C:13]([CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11]=1[C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 221071632-(4-Methylsulfonylphenyl)-1-phenylazulene

Product 1

HCID 221071651-Bromo-2-(4-methylsulfonylphenyl)-3-phenylazuleneYield 99.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-(4-methylsulfonylphenyl)-1-phenylazulene (0.43 g) in CCl4 (20.0 ml) was added N-bromosuccinimide (0.23 g) and α,α'-azobis(isobutyronitrile) (0.01 g), and the reaction mixture was heated under reflux for 1 hr. The mixture was cooled to room temperature and was filtered, and concentrated. The crude product was purified by SiO2 column chromatography (benzene/EtOAc, 20:1) to give the title compound (0.52 g) as green crystals; mp 172°-173° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 1 hr
  3. filtrationwas filtered
  4. concentrationconcentrated
  5. customThe crude product was purified by SiO2 column chromatography (benzene/EtOAc, 20:1)

Sources & evidence

ORD record
ord-ca80cb2be8884ab090ecc4148b601055
Source dataset
uspto-grants-1998_12
Patent number
US05843999

Reaction notes

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