2,6-Dinitrotoluene → 4-Bromo-2,6-dinitrotoluene

HRID 618257Notes

Reaction equation

HRID 618257 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Br:14]([O-])(=O)=O.[K+]>S(=O)(=O)(O)O.O>[Br:14][C:5]1[CH:4]=[C:3]([N+:11]([O-:13])=[O:12])[C:2]([CH3:1])=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=1

Participants

4

Reactant 2

HCID 118132,6-DinitrotolueneHCID 23673461Potassium Bromate

Product 1

HCID 134431864-Bromo-2,6-dinitrotolueneYield 37%

Reagents, catalysts & solvents 1

HCID 21910475Sulfuric acid hydrate (1:1)Solvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-methyl-1,3-dinitro-benzene (10 g) and 1:1 concentrated sulfuric acid-water (100 mL) at 80° C. was added potassium bromate (10.1 g) portionwise over 2-21/2 hr. The mixture was stirred at 80° C. for an additional 2 hr and cooled to room temperature. The mixture was poured into 500 g ice and then extracted with diethyl ether (300 mL). The ether layer was washed with 10% sodium bicarbonate solution (250 mL), brine and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (4:96) to afford 5-bromo-2-methyl-1,3-dinitro-benzene (5.3 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with diethyl ether (300 mL)
  3. washThe ether layer was washed with 10% sodium bicarbonate solution (250 mL), brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (4:96)

Sources & evidence

ORD record
ord-5d8f6e8de4934d219729001ff29cc31f
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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