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

HRID 2208730Notes

Reaction equation

HRID 2208730 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). The precipitate was collected by filtration to give the desired compound (21 g, 98.22%).

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. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-d915b79fc48144c3b0f1859e6a8c5f0c
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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