1,3-Dibromo-5,5-dimethylhydantoin → 5-Bromo-2-methyl-3-nitrobenzoic acid

HRID 2208770Notes

Reaction equation

HRID 2208770 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:14]N1C(C)(C)C(=O)N(Br)C1=O>OS(O)(=O)=O>[Br:14][C:8]1[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]([CH3:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 160962-Methyl-3-nitrobenzoic acid

Product 1

HCID 137700085-Bromo-2-methyl-3-nitrobenzoic acidYield 181.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To stirred solution of 2-methyl-3-nitrobenzoic acid (50 g, 276.2 mmol) in conc. H2SO4 (200 mL), 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione (43.4 g, 151.8 mmol) was added portion wise at room temperature and reaction mass was stirred at room temperature for 5 h. On completion, reaction mixture was poured onto ice cold water, solid precipitated was filtered, resulting residue was washed with water and dried under vacuum giving desired compound (71.7 g, 100%) which was used as is in subsequent steps.

Workup

  1. additionwas added portion wise at room temperature
  2. customreaction mass
  3. customOn completion, reaction mixture
  4. additionwas poured onto ice cold water, solid
  5. customprecipitated
  6. filtrationwas filtered
  7. customresulting residue
  8. washwas washed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-448f043db323406e81ac613a4ca8d9d1
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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