1,3-Dibromo-5,5-dimethylhydantoin → 1-Bromo-3,5-dinitrobenzene

HRID 64082

Reaction equation

HRID 64082 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)([O-:3])=[O:2].[Br:13]N1C(C)(C)C(=O)N(Br)C1=O>S(=O)(=O)(O)O>[Br:13][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[CH:7]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 74521,3-Dinitrobenzene

Product 1

HCID 445341-Bromo-3,5-dinitrobenzeneYield 87%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 1,3-dinitrobenzene (25 g, 0.149 mol) in concentrated sulfuric acid (100 ml) at 0° C. was added 1,3-dibromo-5,5-dimethylhydantoin (31.75 g, 0.111 mol, 0.75 eq) portionwise over a period of 30 min. The mixture was stirred for 12 at RT and quenched by the addition of crushed ice. The precipitate formed was filtered and was washed repeatedly with water to obtain white solid. The solid was dried under vacuum to give the product in 87% yield (32 g).

Workup

  1. customquenched by the addition of crushed ice
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwas washed repeatedly with water
  5. customto obtain white solid
  6. customThe solid was dried under vacuum
  7. customto give the product in 87% yield (32 g)

Sources & evidence

ORD record
ord-f1f8d9b2cac248a29d37c63b1939fb42
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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