Hydrochloric Acid → methyl 4-amino-2-bromobenzoate

HRID 1527445Notes

Reaction equation

HRID 1527445 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[Br:13].[Sn].Cl>CO>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[Br:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 15833211Methyl 2-Bromo-4-nitrobenzoate

Product 1

HCID 5244418methyl 4-amino-2-bromobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-bromo-4-nitro-benzoic acid methyl ester [100959-22-6] (350 mg, 1.35 mmol) in MeOH (60 mL) were subsequently added tin powder (1.6 g, 13.5 mmol) and 3N aqueous HCl (27.8 mL, 83 mmol). The mixture was stirred overnight at RT. The liquid phase was decanted from the excess tin and neutralized by adding a saturated aqueous NaHCO3 solution. An equal amount of water by volume was added and the water phase was extracted with EtOAc (3×). The combined organics were dried (Phase Separator) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (eluent: EtOAc/c-hexane 1:4) to give the title compound as yellow solid. MS (LC/MS): 230 [M+H]+; tR (HPLC conditions b): 2.89 min.

Workup

  1. customThe liquid phase was decanted from the excess tin
  2. additionby adding a saturated aqueous NaHCO3 solution
  3. additionAn equal amount of water by volume was added
  4. extractionthe water phase was extracted with EtOAc (3×)
  5. customThe combined organics were dried (Phase Separator)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel (eluent: EtOAc/c-hexane 1:4)

Sources & evidence

ORD record
ord-0dab0a53b243425f81b81a4c132e5105
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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