Ethanol → ethyl 2-amino-5-bromobenzoate

HRID 2083991Notes

Reaction equation

HRID 2083991 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-50397c609d374c90a14d7ee352e47072
Source dataset
uspto-grants-2004_04
Patent number
US06716841B2

Reaction notes

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