N-bromobutanimide → Methyl 2-amino-5-bromo-4-chlorobenzoate

HRID 1505742Notes

Reaction equation

HRID 1505742 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:13]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([Br:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 80001Methyl 4-chloroanthranilate

Product 1

HCID 53436879Methyl 2-amino-5-bromo-4-chlorobenzoateYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-amino-4-chlorobenzoate (20.0 g, 108 mmol) in DMF (200 mL) was added N-bromosuccinimide (19.2 g, 108 mmol) in one portion and stirred overnight at room temperature. The resulting solids were filtered off and dissolved in toluene, dried with Na2SO4, and concentrated to give methyl 2-amino-5-bromo-4-chlorobenzoate (26.47 g, 93%)

Workup

  1. filtrationThe resulting solids were filtered off
  2. dissolutiondissolved in toluene
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ade5447312274da48b7a0fbe00c901fc
Source dataset
uspto-grants-2015_12
Patent number
US09217004B2

Reaction notes

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