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

HRID 2208687Notes

Reaction equation

HRID 2208687 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 acid

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. Then reaction mixture was slowly poured in to 400 mL of ice cold water. Solid that precipitated out was filtered, washed and dried under vacuum the desired compound (21 g, 98.22%).

Workup

  1. additionwas added
  2. customreaction mixture
  3. customThen reaction mixture
  4. customSolid that precipitated out
  5. filtrationwas filtered
  6. washwashed
  7. dry with materialdried under vacuum the desired compound (21 g, 98.22%)

Sources & evidence

ORD record
ord-21e28f3faf63474b90c7c2ffc9216ed7
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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