Potassium Acetate → 2-Bromo-6-nitrobenzyl Acetate

HRID 459795

Reaction equation

HRID 459795 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH2:11]Br.[CH3:13][C:14]([O-:16])=[O:15].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH2:11][O:16][C:14](=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 150631701-Bromo-2-(bromomethyl)-3-nitrobenzene

Product 1

HCID 588241222-Bromo-6-nitrobenzyl Acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-bromo-2-bromomethyl-3-nitro-benzene (3.39 g, 11.53 mmol) in DMF (50 nml) was added KOAc (7.6 g, 77.4 mmol). The reaction was heated at 70° C. for an hour. After cooling to room temperature, the mixture was partitioned between water and ethyl acetate. The organic layer was washed with water and brine, and dried over MgSO4 Acetic acid 2-bromo-6-nitro-benzyl ester (3.1 g) was obtained as a brown oil after concentration under vacuum (˜100%). 1H NMR (CDCl3, 300 MHz) δ: 2.06(s, 3H), 5.46 (s, 2H), 7.377(t, J=8.1 Hz), 7.778(dd, J=1.23 Hz, 8.14 Hz), 7.856(dd, J=1.23 Hz, 8.07 Hz).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4 Acetic acid 2-bromo-6-nitro-benzyl ester (3.1 g)
  5. customwas obtained as a brown oil
  6. concentrationafter concentration under vacuum (˜100%)

Sources & evidence

ORD record
ord-2b245187379b4f5c91e535abb54e0584
Source dataset
uspto-grants-2007_03
Patent number
US07196087B2

Linked notes

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