Sulfuric Acid → 5-Bromo-2-methyl-3-nitrobenzoic acid

HRID 1351745Notes

Reaction equation

HRID 1351745 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].OS(O)(=O)=O.[Br:19]N1C(C)(C)C(=O)N(Br)C1=O>O>[Br:19][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

5

Reactant 3

HCID 1118Sulfuric AcidHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 160962-Methyl-3-nitrobenzoic acid

Product 1

HCID 137700085-Bromo-2-methyl-3-nitrobenzoic acidYield 184%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 5000 mL, three neck round bottom flask (RBF) equipped with an overhead stirrer was charged with 2-methyl-3-nitro benzoic acid (150.0 g, 0.82 mol) and concentrated H2SO4 (600 mL). To this solution was added 1,3-dibromo-5,5 dimethylhydantoin (130.7 g, 0.455 mol) over ten minutes with vigorous stirring. The reaction was vigorously stirred at ambient temperature for 5 hours. The reaction mixture was then added to water (4000 mL), and the mixture was cooled in an ice bath over 30 minutes. This mixture was then filtered, and the solids were washed twice with water and further dried under vacuum to yield 217.7 g (99.8%) of an off-white solid. 1H NMR (CDCl3) δ 8.18 (s, 1H), 7.95 (s, 1H), 2.59 (s, 3H).

Workup

  1. customA 5000 mL, three neck round bottom flask (RBF) equipped with an overhead stirrer
  2. temperaturethe mixture was cooled in an ice bath over 30 minutes
  3. filtrationThis mixture was then filtered
  4. washthe solids were washed twice with water
  5. customfurther dried under vacuum

Sources & evidence

ORD record
ord-1d72dc7b9cd5459289a6ffe87fa8188f
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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