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

HRID 2208927Notes

Reaction equation

HRID 2208927 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 (50.0 g, 276 mmol) in conc. H2SO4 (200 mL) was added 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione (43.4 g, 151.8 mmol) portion-wise at room temperature and the reaction mixture was stirred at room temperature for 5 h. On completion, the reaction mixture was poured on ice cold water, the resulting precipitate was filtered, washed with water, and dried under vacuum giving desired crude title compound (71.7 g, 99.9%) which was used directly in the next step.

Workup

  1. additionOn completion, the reaction mixture was poured on ice cold water
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e21e1de72acd4e37a4aeba2a34379242
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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