Potassium Acetate → 2-Bromo-6-nitrobenzyl Acetate

HRID 901869Notes

Reaction equation

HRID 901869 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 AcetateYield 98.1%

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 ml) 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

Sources & evidence

ORD record
ord-bb5bfffc647e4565b82f7b6047c24c57
Source dataset
uspto-grants-2008_04
Patent number
US07365063B2

Reaction notes

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