Water → Benzyl 2-bromo-5-nitrobenzoate

HRID 2103750Notes

Reaction equation

HRID 2103750 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(Br)C1C=CC=CC=1>[CH2:4]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[Br:1])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 2430252-Bromo-5-nitrobenzoic acid

Product 1

HCID 19038758Benzyl 2-bromo-5-nitrobenzoateYield 187.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7498Benzyl BromideSolvent

Procedure

Under an atmosphere of argon, to a solution of 2-bromo-5-nitrobenzoic acid (5.14 g) in DMF, benzyl bromide (2.73 mL) and potassium carbonate (4.33 g) were added. The mixture was stirred for 30 minutes at room temperature. To the reaction mixture, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated. The residue was washed with hexane/ethyl acetate to give the title compound (6.59 g) having the following physical data.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe residue was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-096c688eeb30442b9eadb70c82d7af4a
Source dataset
uspto-grants-2009_08
Patent number
US07576129B2

Reaction notes

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