alpha-Bromo-2-nitrotoluene → (2-Nitrophenyl)methyl acetate

HRID 1854522Notes

Reaction equation

HRID 1854522 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10].[C:12]([O-:15])(=[O:14])[CH3:13].[K+]>CN(C=O)C>[C:12]([O:15][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 77569alpha-Bromo-2-nitrotoluene2×HCID 517044Potassium Acetate

Product 1

HCID 131771(2-Nitrophenyl)methyl acetateYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

The mixture of 1-(bromomethyl)-2-nitrobenzene dimer 59 (0.43 g, 1 mmol) and potassium acetate (0.4 g, 4 mmol) in anhydrous DMF (40 mL) was stirred at 70° C. for 6 h, and cooled to r. t. After evaporation, the residue was dispensed with ice-water, and extracted with EtOAc. The combined organic phase was washed with H2O, brine, respectively, and dried over anhydrous Na2SO4. After removing solvent, the crude product was purified by flash column chromatography (elution, hexane/EtOAc:3/1) to yield compound 62 (0.34 g, 88%) as white solid.

Workup

  1. temperaturecooled
  2. customAfter evaporation
  3. extractionextracted with EtOAc
  4. washThe combined organic phase was washed with H2O, brine
  5. dry with materialrespectively, and dried over anhydrous Na2SO4
  6. customAfter removing solvent
  7. customthe crude product was purified by flash column chromatography (elution, hexane/EtOAc:3/1)

Sources & evidence

ORD record
ord-89fd72c6c5b5430897215279a9777424
Source dataset
uspto-grants-2015_02
Patent number
US08962670B2

Reaction notes

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