Ethyl Acetate → 2-(2-Bromoacetyl)-6-nitro-benzoic acid methyl ester

HRID 2251861Notes

Reaction equation

HRID 2251861 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:13](=[O:15])[CH3:14].[Br:17]C1(Br)C(=O)NC(=O)NC1=O.CCOC(C)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:13](=[O:15])[CH2:14][Br:17]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 948775,5-Dibromobarbituric acidHCID 59644399Methyl 2-acetyl-6-nitrobenzoate

Product 1

HCID 596443972-(2-Bromoacetyl)-6-nitro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 2-acetyl-6-nitro-benzoic acid methyl ester (8.20 g, 36.7 mmol, Step C) and 5,5-dibromobarbituric acid (7.35 g, 25.7 mmol) in 200 mL of THF was heated to reflux under N2 for 64 h. The solvents were removed, and the residue was partitioned between EtOAc and Na2CO3(aq). The organic portion was dried over MgSO4, filtered, condensed, and the titled compound was obtained as a white solid after flash column chromatography (5 to 20% of EtOAc in hexanes).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 64 h
  3. customThe solvents were removed
  4. customthe residue was partitioned between EtOAc and Na2CO3(aq)
  5. dry with materialThe organic portion was dried over MgSO4
  6. filtrationfiltered
  7. customcondensed

Sources & evidence

ORD record
ord-3016cb3c6a6a48d39e7b9ac70ffe8a63
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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