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

HRID 1280187Notes

Reaction equation

HRID 1280187 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 and 23.8 g (52%) of the title compound was obtained.

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-d2cf45233e014d7ab445af6fdb2e76ed
Source dataset
uspto-grants-2002_09
Patent number
US06448429B1

Reaction notes

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