Ethanol → ethyl 2-amino-5-bromobenzoate

HRID 2301952Notes

Reaction equation

HRID 2301952 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH2:17](O)[CH3:18]>>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:17][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 798582-Amino-5-bromobenzoic acid

Product 1

HCID 1515283ethyl 2-amino-5-bromobenzoate

Procedure

2-Amino-5-bromobenzoic acid (24.7 g, 11.4 mol) was dissolved in 350 mL of ethanol and 2, and 5 mL of concentrated H2SO4 was added. The mixture was refluxed under N2 for 12 h. The solvent was removed and the residue was added with EtOAc. The mixture was extracted with 1N NaOH. The organic solution was washed with brine, dried over MgSO4. It was concentrated and chromatographed with CH2Cl2 to give 3.19 g of 2-amino-5-bromobenzoic acid, ethyl ester. MS (AP+): 243.9, 246, M+H.

Workup

  1. temperatureThe mixture was refluxed under N2 for 12 h
  2. customThe solvent was removed
  3. additionthe residue was added with EtOAc
  4. extractionThe mixture was extracted with 1N NaOH
  5. washThe organic solution was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationIt was concentrated
  8. customchromatographed with CH2Cl2

Sources & evidence

ORD record
ord-223d4e46cca2476ab48b26a9ec9066c9
Source dataset
uspto-grants-2002_08
Patent number
US06429205B1

Reaction notes

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