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

HRID 473555Notes

Reaction equation

HRID 473555 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-9f457fa5fbf54783b0948cfdf9046db7
Source dataset
uspto-grants-2014_01
Patent number
US08637490B2

Reaction notes

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