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

HRID 2208913Notes

Reaction equation

HRID 2208913 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 181.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To stirred solution of compound 2-methyl-3-nitrobenzoic acid (50.0 g, 276 mmol) in conc. H2SO4 (200 mL), 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione (43.4 g, 152 mmol) was added portionwise at room temperature and stirring was continued for 5 h. On completion, the reaction mass was poured on ice cold water, the solid precipitate was filtered, washed with water and dried under vacuum giving the crude title compound (71.7 g, 99.9%) which was used without further purification.

Workup

  1. additionwas added portionwise at room temperature
  2. additionOn completion, the reaction mass was poured on ice cold water
  3. filtrationthe solid precipitate was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2632b5c557eb48248f2c5fda9a9301e9
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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