Ethanol → Ethyl 5-bromo-2-hydroxybenzoate

HRID 1935985Notes

Reaction equation

HRID 1935985 reaction equation
[Br:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:8][C:7](=[O:9])[C:6]1[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=1)[OH:11])[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 69725-Bromosalicylic acid

Product 1

HCID 4416107Ethyl 5-bromo-2-hydroxybenzoate

Procedure

To 5-bromosalicylic acid (25 g, 115 mmol) in ethyl alcohol (300 mL) was added sulfuric acid (98%, 2 mL). The mixture was refluxed in a Dean-Stark apparatus for 2 days. The reaction mixture was cooled to room temperature. Most of the ethyl alcohol was removed by distillation. The residue was diluted with ethyl acetate, washed with water, aq. Na2CO3 and brine. The organic layer was dried (Na2SO4) and the solvent was removed to afford the title compound as a white solid.

Workup

  1. temperatureThe mixture was refluxed in a Dean-Stark apparatus for 2 days
  2. customMost of the ethyl alcohol was removed by distillation
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water, aq. Na2CO3 and brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-0bee2912e12a46568323a9d53b3fe31c
Source dataset
uspto-grants-2002_05
Patent number
US06388105B1

Reaction notes

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