Azobisisobutyronitrile → 2-Bromo-4-(bromomethyl)benzoic acid

HRID 1371034Notes

Reaction equation

HRID 1371034 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>ClCCCl>[Br:1][C:2]1[CH:10]=[C:9]([CH2:11][Br:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 2262922-Bromo-4-methylbenzoic acid

Product 1

HCID 151299312-Bromo-4-(bromomethyl)benzoic acidYield 52%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-Bromo-4-methylbenzoic acid (33.5 g, 156 mmol, 1 eq) and N-Bromosuccinimide (40.7 g, 233 mmol, 1.5 eq) were dissolved in refluxing 1,2-dichloroethane (600 ml) and a catalytic amount of AIBN was added. The mixture was left stirring under a lamp and under nitrogen for 1 hour. The solvent was removed and the mixture was partitioned between 600 ml of water and 600 ml EtOAc. The organic layer was washed twice with water (600 ml), washed once with brine (600 ml) and then dried with sodium sulfate. The solvent was removed and the crude mixture was triturated with 10% EtOAc/Hexane for 2 hours to give 23.8 g (52%) of the title compound.

Workup

  1. waitThe mixture was left
  2. customThe solvent was removed
  3. customthe mixture was partitioned between 600 ml of water and 600 ml EtOAc
  4. washThe organic layer was washed twice with water (600 ml)
  5. washwashed once with brine (600 ml)
  6. dry with materialdried with sodium sulfate
  7. customThe solvent was removed
  8. customthe crude mixture was triturated with 10% EtOAc/Hexane for 2 hours

Sources & evidence

ORD record
ord-eb949cb4a8be4c6f96cc4b40d38998f2
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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