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

HRID 1427440Notes

Reaction equation

HRID 1427440 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-55cb783e6f5c435e9bdadfa02fd9e1b9
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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