Sodium Sulfate → Methyl 3-amino-4-bromobenzoate

HRID 746766

Reaction equation

HRID 746766 reaction equation
[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:8][O:9][C:10](=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[C:13]([N+:18]([O-])=O)[CH:12]=1>CCO>[CH3:8][O:9][C:10](=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[C:13]([NH2:18])[CH:12]=1

Participants

4

Reactant 2

HCID 24436Sodium SulfateHCID 2736829Methyl 4-bromo-3-nitrobenzoate

Product 1

HCID 3928639Methyl 3-amino-4-bromobenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add Na2SO4(8.5 mmol) to a solution of 4-Bromo-3-nitro-benzoic acid methyl ester (1.2 mmol) in EtOH (40 mL). Heat the reaction at 70° C. for 30 min and then at room temperature overnight. Add a saturated solution of NaHCO3(pH=11-12) and extract with EtOAc (2×50 mL). Dry over NaSO4, filter and evaporate to dryness to provide 4-Bromo-3-amino-benzoic acid methyl ester.

Workup

  1. temperatureHeat
  2. customthe reaction at 70° C. for 30 min
  3. customat room temperature
  4. customovernight
  5. additionAdd a saturated solution of NaHCO3(pH=11-12)
  6. extractionextract with EtOAc (2×50 mL)
  7. dry with materialDry over NaSO4
  8. filtrationfilter
  9. customevaporate to dryness

Sources & evidence

ORD record
ord-3b095d2307594cbe8bfd0785c20ee747
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Linked notes

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