2,6-Dimethyl-4-nitrophenyl trifluoromethanesulfonate → 2-Bromo-1,3-dimethyl-5-nitrobenzene

HRID 2406935Notes

Reaction equation

HRID 2406935 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=1[CH3:17])(=O)=O.O.[Br-:21].[Li+]>CN(C)C=O.[Cl-].[NH4+]>[Br:21][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=1[CH3:17]

Participants

5

Reactant 2

HCID 226621252,6-Dimethyl-4-nitrophenyl trifluoromethanesulfonateHCID 23702478Lithium bromide hydrate

Product 1

HCID 70220962-Bromo-1,3-dimethyl-5-nitrobenzeneYield 69%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

2,6-dimethyl-4-nitrophenyl trifluoromethanesulfonate (5.0 g, 17 mmol) was dissolved in N,N-dimethylformamide (40 mL). Lithium bromide monohydrate (4.7 g, 45 mmol) was added and the reaction was refluxed overnight. The reaction was diluted with saturated ammonium chloride and the layers were separated. The organics were washed with water (3×40 mL) and brine, dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (2% ethyl acetate in petroleum ether) gave 2-bromo-1,3-dimethyl-5-nitrobenzene (2.7 g, 69%) as a light yellow solid. 1H NMR (400 MHz, CDCl3, δ): 7.94 (s, 2H), 2.50 (s, 6H).

Workup

  1. temperaturethe reaction was refluxed overnight
  2. customthe layers were separated
  3. washThe organics were washed with water (3×40 mL) and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-2f994363315c41feb559c9f3e9078c96
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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