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

HRID 1501653Notes

Reaction equation

HRID 1501653 reaction equation
[Br:1]N1C(C)(C)C(=O)N(Br)C1=O.[CH3:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]>OS(O)(=O)=O>[Br:1][C:19]1[CH:20]=[C:21]([N+:22]([O-:24])=[O:23])[C:13]([CH3:12])=[C:14]([CH:18]=1)[C:15]([OH:17])=[O:16]

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 176.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione (13.0 g, 45.7 mmol) was added to a mixture of 2-methyl-3-nitrobenzoic acid (15 g, 82.8 mmol) in conc. H2SO4 (60 mL), and the reaction mixture stirred at room temperature for 5 h. After completion of reaction, the mixture was slowly poured onto ice cold water (400 mL). The precipitated was filtered and dried under vacuum to obtain desired 5-bromo-2-methyl-3-nitrobenzoic acid (21 g, 98.2%).

Workup

  1. customAfter completion of reaction
  2. additionthe mixture was slowly poured onto ice cold water (400 mL)
  3. filtrationThe precipitated was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-439d3bc81aa14f51ae9213dc251c872d
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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