Benzoyl Peroxide → HCID 22648203, compound

HRID 394141Notes

Reaction equation

HRID 394141 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:3]=1[CH3:16].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:3]=1[CH2:16][Br:17]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 226481954,6-Dibromo-2-(2-chlorophenyl)-3-methylpyridine

Product 1

HCID 22648203HCID 22648203, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a suspension of 6.3 g of 4,6-dibromo-2-(2-chlorophenyl)-3-methylpyridine (COMPOUND W-1) in 75 mL of CCl4 was added 3.7 g of N-bromosuccinimide and 420 mg of benzoyl peroxide. The mixture was heated to reflux and stirred at this temperature for 6 h, then cooled and concentrated. The residue was dissolved in 150 mL of 1:1 hexanes-Et2O and filtered through a pad of silica gel, then purified in two batches by flash chromatography on Biotage 40M columns, eluting with a gradient system of 99:1 to 97:3 hexanes-Et2O, to yield the title compound as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturecooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 150 mL of 1:1 hexanes-Et2O
  6. filtrationfiltered through a pad of silica gel
  7. custompurified in two batches by flash chromatography on Biotage 40M columns
  8. washeluting with a gradient system of 99:1 to 97:3 hexanes-Et2O

Sources & evidence

ORD record
ord-258a4e1b82c84b9380e48bdac39f1574
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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