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

HRID 1616487Notes

Reaction equation

HRID 1616487 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 175%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To stirred solution of 2-methyl-3-nitrobenzoic acid (100 g, 552.48 mmol) in conc. H2SO4 (400 mL), 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione (87.98 g, 307.70 mmol) was added in a portion-wise manner at room temperature. The reaction mixture was then stirred at room temperature for 5 h. The reaction mixture was poured into ice cold water, the precipitated solid collected by filtration, washed with water and dried under vacuum to afford desired 5-bromo-2-methyl-3-nitrobenzoic acid as off-white solid (140 g, 97.90% yield). 1H NMR (DMSO-d6, 400 MHz) δ 8.31 (s, 1H), 8.17 (s, 1H), 2.43 (s, 3H).

Workup

  1. additionwas added in a portion-wise manner at room temperature
  2. additionThe reaction mixture was poured into ice cold water
  3. filtrationthe precipitated solid collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4b01adbd09944785947e310e1d8b63da
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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