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

HRID 2208742Notes

Reaction equation

HRID 2208742 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 176.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a mixture of 2-methyl-3-nitrobenzoic acid (15 g, 82.80 mmol) in conc. H2SO4 (60 mL), 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione (13.07 g, 45.71 mmol) was added and reaction mixture was stirred at room temperature for 5 h. After completion of reaction, reaction mixture was slowly poured onto ice cold water (400 mL). Solid that precipitated out was filtered and dried under vacuum to obtain the desired compound (21 g, 98%).

Workup

  1. additionwas added
  2. customreaction mixture
  3. customAfter completion of reaction, reaction mixture
  4. additionwas slowly poured onto ice cold water (400 mL)
  5. customSolid that precipitated out
  6. filtrationwas filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-752e353953bd44618fb4da86986133bf
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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