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

HRID 1530223Notes

Reaction equation

HRID 1530223 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 181.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution, of 2-methyl-3-nitrobenzoic acid (50 g, 276.2 mmol) in conc. H2SO4 (200 mL) was added 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione (43.4 g, 151.8 mmol) portion wise at room temperature and the reaction mixture was stirred at room temperature for 5 h. On completion, the reaction mixture was poured onto ice cold water, the resulting precipitate was filtered, the residue was washed with water and dried under vacuum to give 5-bromo-2-methyl-3-nitrobenzoic acid (71.7 g, 99.9%) which was used directly in the next step.

Workup

  1. additionOn completion, the reaction mixture was poured onto ice cold water
  2. filtrationthe resulting precipitate was filtered
  3. washthe residue was washed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-59e472ca5e1c4a70bbf15f401f137eb0
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

Loading…