Ethanol → Ethyl 4-bromo-3-hydroxybenzoate

HRID 2100374Notes

Reaction equation

HRID 2100374 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:17][CH3:18])=[O:7])=[CH:4][C:3]=1[OH:11]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 64209734-Bromo-3-hydroxybenzoic acid

Product 1

HCID 12134897Ethyl 4-bromo-3-hydroxybenzoate

Procedure

4-Bromo-3-hydroxybenzoic acid (100 mg) was dissolved in absolute ethanol (10 ml) and concentrated sulfuric acid (60 μl) added. The reaction was heated at reflux under nitrogen for 22 hours. The solvent was evaporated and the residue was partitioned between ethyl acetate/chloroform (1:1) and water. The organic layers were combined, dried using a hydrophobic filter and the solvent evaporated leaving ethyl 4-bromo-3-hydroxybenzoate as a white solid (109 mg).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux under nitrogen for 22 hours
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between ethyl acetate/chloroform (1:1) and water
  5. customdried
  6. filtrationa hydrophobic filter
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-5dfc95da70c343029ba119c9f683b134
Source dataset
uspto-grants-2009_08
Patent number
US07572790B2

Reaction notes

Loading…